BE525396A - - Google Patents
Info
- Publication number
- BE525396A BE525396A BE525396DA BE525396A BE 525396 A BE525396 A BE 525396A BE 525396D A BE525396D A BE 525396DA BE 525396 A BE525396 A BE 525396A
- Authority
- BE
- Belgium
- Prior art keywords
- pyrimidine
- hydroxy
- hydrogen
- preparation
- diamino
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-Diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 230000002378 acidificating Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-amino-1H-pyrimidine-2,4-dione Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 238000002844 melting Methods 0.000 description 15
- 235000011007 phosphoric acid Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- YRKCREAYFQTBPV-UHFFFAOYSA-N Acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- -1 7-substituted pyrido- (2,3-d) -pyrimidines Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004989 dicarbonyl group Chemical group 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- SYQZVEHCTPWQBQ-UHFFFAOYSA-N 2-ethyl-3-oxohexanal Chemical compound CCCC(=O)C(CC)C=O SYQZVEHCTPWQBQ-UHFFFAOYSA-N 0.000 description 1
- FCYLEYQOYIWKLA-UHFFFAOYSA-N 2-methyl-3-oxo-3-phenylpropanal Chemical compound O=CC(C)C(=O)C1=CC=CC=C1 FCYLEYQOYIWKLA-UHFFFAOYSA-N 0.000 description 1
- BPPPUFSZQDCMEE-UHFFFAOYSA-N 2-oxocyclohexane-1-carbaldehyde Chemical compound O=CC1CCCCC1=O BPPPUFSZQDCMEE-UHFFFAOYSA-N 0.000 description 1
- ZAIBWUAGAZIQMM-UHFFFAOYSA-N 2-oxocyclopentane-1-carbaldehyde Chemical compound O=CC1CCCC1=O ZAIBWUAGAZIQMM-UHFFFAOYSA-N 0.000 description 1
- OQUIKKDRNCXZTQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-oxopropanal Chemical compound ClC1=CC=C(C(=O)CC=O)C=C1 OQUIKKDRNCXZTQ-UHFFFAOYSA-N 0.000 description 1
- HCSDAMGBOVWGEO-UHFFFAOYSA-N 3-oxo-3-phenylpropanal Chemical compound O=CCC(=O)C1=CC=CC=C1 HCSDAMGBOVWGEO-UHFFFAOYSA-N 0.000 description 1
- 150000005007 4-aminopyrimidines Chemical group 0.000 description 1
- BPJWGHJLUSXUFE-UHFFFAOYSA-N 5,7-dimethyl-2-sulfanylidene-1H-pyrido[2,3-d]pyrimidin-4-one Chemical compound N1C(=S)NC(=O)C=2C1=NC(C)=CC=2C BPJWGHJLUSXUFE-UHFFFAOYSA-N 0.000 description 1
- BLOCGUWRFAOSFW-UHFFFAOYSA-N 6-amino-5H-pyrimidine-2,4-dione Chemical compound NC1=NC(=O)NC(=O)C1 BLOCGUWRFAOSFW-UHFFFAOYSA-N 0.000 description 1
- AIZDQOJUSOTWDD-UHFFFAOYSA-N 7-phenylpyrido[2,3-d]pyrimidine Chemical compound C1=CC=CC=C1C1=CC=C(C=NC=N2)C2=N1 AIZDQOJUSOTWDD-UHFFFAOYSA-N 0.000 description 1
- KMCRISSMMQKYTQ-UHFFFAOYSA-N ClC=1N=C(C2=C(N1)N=C(C(=C2C)C)C)Cl Chemical compound ClC=1N=C(C2=C(N1)N=C(C(=C2C)C)C)Cl KMCRISSMMQKYTQ-UHFFFAOYSA-N 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N Dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 229960000304 Folic Acid Drugs 0.000 description 1
- 102100009854 MID1 Human genes 0.000 description 1
- 101700079340 MID1 Proteins 0.000 description 1
- BBOHRUBZIMRNFH-UHFFFAOYSA-N OC=1N=C(C2=C(N1)N=C(C(=C2C)C)C)O Chemical compound OC=1N=C(C2=C(N1)N=C(C(=C2C)C)C)O BBOHRUBZIMRNFH-UHFFFAOYSA-N 0.000 description 1
- AWXCWJNJONXHQZ-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C(=C2)C)CC)O Chemical compound SC=1N=C(C2=C(N1)N=C(C(=C2)C)CC)O AWXCWJNJONXHQZ-UHFFFAOYSA-N 0.000 description 1
- PWCXCLOQSYHZKL-UHFFFAOYSA-N SC=1N=C(C2=C(N1)N=C(C=C2)C2=CC=CC=C2)O Chemical compound SC=1N=C(C2=C(N1)N=C(C=C2)C2=CC=CC=C2)O PWCXCLOQSYHZKL-UHFFFAOYSA-N 0.000 description 1
- ZWVWPLDYRKSPJF-UHFFFAOYSA-N SC=1N=C(C2=C(N=1)N=C(C(=C2)C(C)C)CC(C)C)O Chemical compound SC=1N=C(C2=C(N=1)N=C(C(=C2)C(C)C)CC(C)C)O ZWVWPLDYRKSPJF-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000670 limiting Effects 0.000 description 1
- 230000002503 metabolic Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- MVDYEFQVZNBPPH-UHFFFAOYSA-N pentane-2,3,4-trione Chemical compound CC(=O)C(=O)C(C)=O MVDYEFQVZNBPPH-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- MWVKGSABHBJPOX-UHFFFAOYSA-N pyridine-2,4,6-triamine Chemical compound NC1=CC(N)=NC(N)=C1 MWVKGSABHBJPOX-UHFFFAOYSA-N 0.000 description 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reduced Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 101710028591 sam1 Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE525396A true BE525396A (xx) |
Family
ID=159706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE525396D BE525396A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE525396A (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2191897A1 (en) * | 1972-07-07 | 1974-02-08 | Hisamitsu Pharmaceutical Co | Pyrido (2,3-d) pyrimidine-(2,4) (1H, 3-H)-diones - antiinflammatories, analgesics and CNS depressants |
-
0
- BE BE525396D patent/BE525396A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2191897A1 (en) * | 1972-07-07 | 1974-02-08 | Hisamitsu Pharmaceutical Co | Pyrido (2,3-d) pyrimidine-(2,4) (1H, 3-H)-diones - antiinflammatories, analgesics and CNS depressants |
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