BE531260A - - Google Patents
Info
- Publication number
- BE531260A BE531260A BE531260DA BE531260A BE 531260 A BE531260 A BE 531260A BE 531260D A BE531260D A BE 531260DA BE 531260 A BE531260 A BE 531260A
- Authority
- BE
- Belgium
- Prior art keywords
- mercapto
- amino
- water
- compound
- mixture
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 mercapto, selenyl Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- RGKLWAHLGYLIKT-UHFFFAOYSA-N 2,3-dihydrotriazolo[4,5-d]pyrimidine-7-thione Chemical compound S=C1N=CN=C2NNN=C12 RGKLWAHLGYLIKT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- NGMMEPMKKHBFDS-UHFFFAOYSA-N 7H-purine-6-selenol Chemical compound [SeH]C1=NC=NC2=C1NC=N2 NGMMEPMKKHBFDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- GNGUIFCJLKENCH-UHFFFAOYSA-N 5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidine-7-thione Chemical compound S=C1N=C(N)N=C2NNN=C21 GNGUIFCJLKENCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 239000000908 ammonium hydroxide Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229960000583 Acetic Acid Drugs 0.000 description 7
- CYQAYERJWZKYML-UHFFFAOYSA-N Phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002285 radioactive Effects 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002019 disulfides Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000001376 precipitating Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KHAZBQMTILVQFT-UHFFFAOYSA-N 8-methyl-3,7-dihydropurin-6-one Chemical compound N1C=NC(=O)C2=C1N=C(C)N2 KHAZBQMTILVQFT-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical class S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
- 125000001442 methylidyne group Chemical group [H]C#[*] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XMSMHKMPBNTBOD-UHFFFAOYSA-N 2-(dimethylamino)-3,7-dihydropurin-6-one Chemical compound N1C(N(C)C)=NC(=O)C2=C1N=CN2 XMSMHKMPBNTBOD-UHFFFAOYSA-N 0.000 description 2
- VXLWZQSFTAUUSA-UHFFFAOYSA-N 2-(dimethylamino)-3,7-dihydropurine-6-thione Chemical compound N1C(N(C)C)=NC(=S)C2=C1N=CN2 VXLWZQSFTAUUSA-UHFFFAOYSA-N 0.000 description 2
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-chloro-7H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M Potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229960001428 mercaptopurine Drugs 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- BKWNMYAKKPLPFE-UHFFFAOYSA-N 2,5,6-triamino-1H-pyrimidine-4-thione Chemical compound NC1=NC(N)=C(N)C(=S)N1 BKWNMYAKKPLPFE-UHFFFAOYSA-N 0.000 description 1
- SOQYJXVHBQVRDB-UHFFFAOYSA-N 2,6-bis(sulfanylidene)-7,9-dihydro-3H-purin-8-one Chemical compound N1C(=S)NC(=S)C2=C1NC(=O)N2 SOQYJXVHBQVRDB-UHFFFAOYSA-N 0.000 description 1
- DPQSMNLSYIBAAG-UHFFFAOYSA-N 2-amino-8-methylsulfanyl-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(SC)N2 DPQSMNLSYIBAAG-UHFFFAOYSA-N 0.000 description 1
- OTLARBCFYJPBDK-UHFFFAOYSA-N 2-methylsulfanyl-3,7-dihydropurin-6-one Chemical compound N1C(SC)=NC(=O)C2=C1N=CN2 OTLARBCFYJPBDK-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- HDSKJRZKLHXPNF-UHFFFAOYSA-M 4-chlorobenzenediazonium;chloride Chemical compound [Cl-].ClC1=CC=C([N+]#N)C=C1 HDSKJRZKLHXPNF-UHFFFAOYSA-M 0.000 description 1
- TVGKPALXOIHHFY-UHFFFAOYSA-N 5-(2H-triazolo[4,5-d]pyrimidin-5-yldisulfanyl)-2H-triazolo[4,5-d]pyrimidine Chemical compound N1=CC2=NNN=C2N=C1SSC1=NC2=NNN=C2C=N1 TVGKPALXOIHHFY-UHFFFAOYSA-N 0.000 description 1
- BWLOHIMQWHFSQF-UHFFFAOYSA-N 6-chloro-5-nitropyrimidin-4-amine Chemical compound NC1=NC=NC(Cl)=C1[N+]([O-])=O BWLOHIMQWHFSQF-UHFFFAOYSA-N 0.000 description 1
- QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloropyrimidine-2,4-diamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 1
- BMLKPGJBYUTIHT-UHFFFAOYSA-N 6-ethoxy-7H-purine Chemical compound CCOC1=NC=NC2=C1NC=N2 BMLKPGJBYUTIHT-UHFFFAOYSA-N 0.000 description 1
- VIVHKHHYZLMJQH-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-6-thione Chemical compound N1C=NC(=S)C2=C1N=C(C)N2 VIVHKHHYZLMJQH-UHFFFAOYSA-N 0.000 description 1
- 210000004185 Liver Anatomy 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ININMFLHQXATDK-UHFFFAOYSA-N OC1=C(N=C2C=NC=NC2=N1)C(=O)O Chemical compound OC1=C(N=C2C=NC=NC2=N1)C(=O)O ININMFLHQXATDK-UHFFFAOYSA-N 0.000 description 1
- LPXQRXLUHJKZIE-UHFFFAOYSA-N Pathocidin Chemical compound NC1=NC(O)=C2NN=NC2=N1 LPXQRXLUHJKZIE-UHFFFAOYSA-N 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N Potassium sulfide Chemical class [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- VPQBLCVGUWPDHV-UHFFFAOYSA-N Sodium selenide Chemical class [Na+].[Na+].[Se-2] VPQBLCVGUWPDHV-UHFFFAOYSA-N 0.000 description 1
- 210000002700 Urine Anatomy 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005122 aminoalkylamino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical class [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 150000003959 diselenides Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 230000000155 isotopic Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZDHURYWHEBEGHO-KNFKBKLISA-N potassium-40;potassium-42 Chemical compound [40K].[42K] ZDHURYWHEBEGHO-KNFKBKLISA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 230000003439 radiotherapeutic Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/36—Sulfur atom
- C07D473/38—Sulfur atom attached in position 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE531260A true BE531260A (zh) |
Family
ID=163659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE531260D BE531260A (zh) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE531260A (zh) |
-
0
- BE BE531260D patent/BE531260A/fr unknown
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