BE561644A - - Google Patents
Info
- Publication number
- BE561644A BE561644A BE561644DA BE561644A BE 561644 A BE561644 A BE 561644A BE 561644D A BE561644D A BE 561644DA BE 561644 A BE561644 A BE 561644A
- Authority
- BE
- Belgium
- Prior art keywords
- solution
- water
- acid
- precipitate
- compounds
- Prior art date
Links
- -1 amide radicals Chemical class 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 24
- 239000000203 mixture Substances 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 14
- 239000002244 precipitate Substances 0.000 claims 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 10
- 239000000047 product Substances 0.000 claims 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 7
- 238000004458 analytical method Methods 0.000 claims 7
- 239000013078 crystal Substances 0.000 claims 7
- JTTIOYHBNXDJOD-UHFFFAOYSA-N 2,4,6-triaminopyrimidine Chemical compound NC1=CC(N)=NC(N)=N1 JTTIOYHBNXDJOD-UHFFFAOYSA-N 0.000 claims 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 5
- 229960000583 acetic acid Drugs 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 238000004364 calculation method Methods 0.000 claims 5
- 239000012362 glacial acetic acid Substances 0.000 claims 5
- 238000002844 melting Methods 0.000 claims 5
- 230000008018 melting Effects 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 5
- 238000003756 stirring Methods 0.000 claims 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000012954 diazonium Substances 0.000 claims 4
- 150000001989 diazonium salts Chemical class 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 4
- 235000010288 sodium nitrite Nutrition 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 238000006149 azo coupling reaction Methods 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 2
- CQXXYOLFJXSRMT-UHFFFAOYSA-N 5-diazocyclohexa-1,3-diene Chemical class [N-]=[N+]=C1CC=CC=C1 CQXXYOLFJXSRMT-UHFFFAOYSA-N 0.000 claims 2
- 241000194032 Enterococcus faecalis Species 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 208000009916 Yoshida Sarcoma Diseases 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- JOPDUWRZRJKLIF-UHFFFAOYSA-N aminooxy(phenyl)phosphinic acid Chemical compound NOP(O)(=O)C1=CC=CC=C1 JOPDUWRZRJKLIF-UHFFFAOYSA-N 0.000 claims 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000001632 sodium acetate Substances 0.000 claims 2
- 235000017281 sodium acetate Nutrition 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 claims 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 claims 1
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 claims 1
- 241000186660 Lactobacillus Species 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- 241000920340 Pion Species 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 208000006268 Sarcoma 180 Diseases 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- 239000000063 antileukemic agent Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 230000021615 conjugation Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 230000002380 cytological effect Effects 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940039696 lactobacillus Drugs 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 229960001428 mercaptopurine Drugs 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 210000005170 neoplastic cell Anatomy 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229940005654 nitrite ion Drugs 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- FWSOTVBYRDKQOQ-UHFFFAOYSA-N phenyl-(2-pyrimidin-2-ylphenyl)diazene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1C1=NC=CC=N1 FWSOTVBYRDKQOQ-UHFFFAOYSA-N 0.000 claims 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 claims 1
- MQWDCWDZUCOIRM-UHFFFAOYSA-N pyrimidine-2,4,6-triamine;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC(N)=NC(N)=N1 MQWDCWDZUCOIRM-UHFFFAOYSA-N 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000001226 reprecipitation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE561644A true BE561644A (en:Method) |
Family
ID=183525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE561644D BE561644A (en:Method) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE561644A (en:Method) |
-
0
- BE BE561644D patent/BE561644A/fr unknown
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