BE561091A - - Google Patents
Info
- Publication number
- BE561091A BE561091A BE561091DA BE561091A BE 561091 A BE561091 A BE 561091A BE 561091D A BE561091D A BE 561091DA BE 561091 A BE561091 A BE 561091A
- Authority
- BE
- Belgium
- Prior art keywords
- compound according
- chemical compound
- methyl
- hydrazino
- aldehyde
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 100
- 150000001299 aldehydes Chemical class 0.000 claims description 82
- -1 nitro, amino Chemical group 0.000 claims description 62
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 12
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical compound NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- JECYUBVRTQDVAT-UHFFFAOYSA-N 1-(2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims description 6
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-Formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 6
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- TXFPEBPIARQUIG-UHFFFAOYSA-N Piceol Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- WTWBUQJHJGUZCY-UHFFFAOYSA-N Cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N methylphenylketone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- WEGYGNROSJDEIW-UHFFFAOYSA-N 1-pyridin-3-ylethanone Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 claims description 3
- FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims description 3
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims description 3
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 claims description 2
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 claims description 2
- BHLZAJPXLXRFAO-UHFFFAOYSA-N 5-aminosalicylaldehyde Chemical compound NC1=CC=C(O)C(C=O)=C1 BHLZAJPXLXRFAO-UHFFFAOYSA-N 0.000 claims description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 230000001225 therapeutic Effects 0.000 claims description 2
- XTRAWORUGOJWSH-UHFFFAOYSA-N 4-methoxy-2-methylpyrimidine Chemical compound COC1=CC=NC(C)=N1 XTRAWORUGOJWSH-UHFFFAOYSA-N 0.000 claims 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-Methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- FFBZGVRBIPBPHE-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)methylidene]hydrazinyl]-6-methyl-1H-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1NN=CC1=CC=CC=C1Cl FFBZGVRBIPBPHE-UHFFFAOYSA-N 0.000 claims 1
- IMVWTINQRZDOGZ-UHFFFAOYSA-N 2-[2-[(2-methoxyphenyl)methylidene]hydrazinyl]-6-methyl-1H-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C=NNC1=NC(=O)C=C(C)N1 IMVWTINQRZDOGZ-UHFFFAOYSA-N 0.000 claims 1
- VHROUCLVTSMYCM-UHFFFAOYSA-N 2-[2-[(4-chlorophenyl)methylidene]hydrazinyl]-6-methyl-1H-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1NN=CC1=CC=C(Cl)C=C1 VHROUCLVTSMYCM-UHFFFAOYSA-N 0.000 claims 1
- KIMPOJXDFKFBTL-UHFFFAOYSA-N 2-[2-[(4-methoxyphenyl)methylidene]hydrazinyl]-6-methyl-1H-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C=NNC1=NC(=O)C=C(C)N1 KIMPOJXDFKFBTL-UHFFFAOYSA-N 0.000 claims 1
- KCMZECCBNACZAX-UHFFFAOYSA-N 2-[[(6-methyl-4-oxo-1H-pyrimidin-2-yl)hydrazinylidene]methyl]benzoic acid Chemical compound N1C(C)=CC(=O)N=C1NN=CC1=CC=CC=C1C(O)=O KCMZECCBNACZAX-UHFFFAOYSA-N 0.000 claims 1
- HHDPXULKSZZACU-UHFFFAOYSA-N 2-hydroxy-4-nitrobenzaldehyde Chemical compound OC1=CC([N+]([O-])=O)=CC=C1C=O HHDPXULKSZZACU-UHFFFAOYSA-N 0.000 claims 1
- DOHOPUBZLWVZMZ-UHFFFAOYSA-N 3-chloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=CC=C1C=O DOHOPUBZLWVZMZ-UHFFFAOYSA-N 0.000 claims 1
- LHRIUKSRPHFASO-UHFFFAOYSA-N 6-methyl-1H-pyrimidin-4-one Chemical compound CC1=CC(=O)N=CN1 LHRIUKSRPHFASO-UHFFFAOYSA-N 0.000 claims 1
- XAAXCKMMGKZWHA-UHFFFAOYSA-N 6-methyl-2-[2-[(2-nitrophenyl)methylidene]hydrazinyl]-1H-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1NN=CC1=CC=CC=C1[N+]([O-])=O XAAXCKMMGKZWHA-UHFFFAOYSA-N 0.000 claims 1
- DNVNCOMWYRMDOB-UHFFFAOYSA-N 6-methyl-2-[2-[(3-nitrophenyl)methylidene]hydrazinyl]-1H-pyrimidin-4-one Chemical compound N1C(C)=CC(=O)N=C1NN=CC1=CC=CC([N+]([O-])=O)=C1 DNVNCOMWYRMDOB-UHFFFAOYSA-N 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 423
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 39
- 238000004458 analytical method Methods 0.000 description 31
- 235000019441 ethanol Nutrition 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 10
- 239000007859 condensation product Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- PCHXNQBTDCVAIT-UHFFFAOYSA-N (4-methoxy-6-methylpyrimidin-2-yl)hydrazine Chemical compound COC1=CC(C)=NC(NN)=N1 PCHXNQBTDCVAIT-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- HXQPYFMXCAIHAB-UHFFFAOYSA-N (4-methoxypyrimidin-2-yl)hydrazine Chemical compound COC1=CC=NC(NN)=N1 HXQPYFMXCAIHAB-UHFFFAOYSA-N 0.000 description 3
- RFKCQKWRFAJRPY-UHFFFAOYSA-N 2-hydrazinyl-6-methyl-1H-pyrimidin-4-one Chemical compound CC1=CC(=O)N=C(NN)N1 RFKCQKWRFAJRPY-UHFFFAOYSA-N 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- 230000001549 tubercolostatic Effects 0.000 description 3
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 2
- VGYDZMSZARMTMH-UHFFFAOYSA-N 2-hydrazinyl-5-methyl-1H-pyrimidin-6-one Chemical compound CC1=CN=C(NN)NC1=O VGYDZMSZARMTMH-UHFFFAOYSA-N 0.000 description 2
- JZEBRWXXXNUMPB-UHFFFAOYSA-N 2-hydrazinyl-6-methylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(NN)=N1 JZEBRWXXXNUMPB-UHFFFAOYSA-N 0.000 description 2
- OTOWPAWAWTZRGE-UHFFFAOYSA-N 4-hydrazinyl-6-methyl-1H-pyrimidin-2-one Chemical compound CC1=CC(NN)=NC(O)=N1 OTOWPAWAWTZRGE-UHFFFAOYSA-N 0.000 description 2
- MWYPVCMVSYPXBW-UHFFFAOYSA-N 4-hydrazinyl-6-methylpyrimidin-2-amine Chemical compound CC1=CC(NN)=NC(N)=N1 MWYPVCMVSYPXBW-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002609 media Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- WUKBRNKMQNEPAW-UHFFFAOYSA-N (4-methylpyrimidin-2-yl)hydrazine Chemical compound CC1=CC=NC(NN)=N1 WUKBRNKMQNEPAW-UHFFFAOYSA-N 0.000 description 1
- QZWHXGZANIHORL-UHFFFAOYSA-N (6-methylpyrimidin-4-yl)hydrazine Chemical compound CC1=CC(NN)=NC=N1 QZWHXGZANIHORL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N 4-Anisaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- OHDMIERTIPXMBO-CFCGPWAMSA-N 5-acetyl-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-2-one Chemical compound O=C1NC(C(=O)C)=CN1[C@@H]1O[C@H](CO)C(O)C1 OHDMIERTIPXMBO-CFCGPWAMSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N Anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 240000008893 Cynodon dactylon Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 229940010383 Mycobacterium tuberculosis Drugs 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-Anisic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- UJTMLNARSPORHR-UHFFFAOYSA-N OC2H5 Chemical group C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 1
- 241001435139 Salia Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000001408 fungistatic Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 201000000526 hyperphosphatemic familial tumoral calcinosis Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000021178 picnic Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE561091A true BE561091A (es) |
Family
ID=183162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE561091D BE561091A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE561091A (es) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006029850A1 (en) * | 2004-09-14 | 2006-03-23 | The Genetics Company, Inc. | Hydrazone derivatives and their use as beta secretase inhibitors |
| EP2311457A1 (en) * | 2009-10-19 | 2011-04-20 | Forschungszentrum Borstel | Pharmaceutical compositions for treating infections with drug resistant mycobacteria |
| US8389718B2 (en) | 2010-07-20 | 2013-03-05 | Vestaron Corporation | Insecticidal triazines and pyrimidines |
| WO2014083095A1 (en) * | 2012-11-29 | 2014-06-05 | Universitaet Basel | Combinations of metformin with other compounds for the treatment of cancer and for immunosuppression |
| EP2762465A1 (en) * | 2011-09-27 | 2014-08-06 | Zeon Corporation | Intermediate for manufacture of polymerizable compound and process for manufacture thereof |
-
0
- BE BE561091D patent/BE561091A/fr unknown
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006029850A1 (en) * | 2004-09-14 | 2006-03-23 | The Genetics Company, Inc. | Hydrazone derivatives and their use as beta secretase inhibitors |
| EP2311457A1 (en) * | 2009-10-19 | 2011-04-20 | Forschungszentrum Borstel | Pharmaceutical compositions for treating infections with drug resistant mycobacteria |
| WO2011047814A1 (en) * | 2009-10-19 | 2011-04-28 | Forschungszentrum Borstel | Pharmaceutical compositions for treating infections with drug resistant mycobacteria |
| US8389718B2 (en) | 2010-07-20 | 2013-03-05 | Vestaron Corporation | Insecticidal triazines and pyrimidines |
| US8785630B2 (en) | 2010-07-20 | 2014-07-22 | Vestaron Corporation | Insecticidal triazines and pyrimidines |
| EP2762465A1 (en) * | 2011-09-27 | 2014-08-06 | Zeon Corporation | Intermediate for manufacture of polymerizable compound and process for manufacture thereof |
| US20140235857A1 (en) * | 2011-09-27 | 2014-08-21 | Zeon Corporation | Intermediate for manufacture of polymerizable compound and process for manufacture thereof |
| US9447059B2 (en) * | 2011-09-27 | 2016-09-20 | Zeon Corporation | Intermediate for manufacture of polymerizable compound and process for manufacture thereof |
| EP2762465B1 (en) * | 2011-09-27 | 2018-01-10 | Zeon Corporation | Intermediate for manufacture of polymerizable compound and process for manufacture thereof |
| WO2014083095A1 (en) * | 2012-11-29 | 2014-06-05 | Universitaet Basel | Combinations of metformin with other compounds for the treatment of cancer and for immunosuppression |
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