IL24642A - Method for preparation of 6-thioxo purines from 6-methylthio purines - Google Patents
Method for preparation of 6-thioxo purines from 6-methylthio purinesInfo
- Publication number
- IL24642A IL24642A IL2464265A IL2464265A IL24642A IL 24642 A IL24642 A IL 24642A IL 2464265 A IL2464265 A IL 2464265A IL 2464265 A IL2464265 A IL 2464265A IL 24642 A IL24642 A IL 24642A
- Authority
- IL
- Israel
- Prior art keywords
- purine
- methyl
- thioxo
- methylthio
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 10
- UIJIQXGRFSPYQW-UHFFFAOYSA-N 6-methylthiopurine Chemical class CSC1=NC=NC2=C1N=CN2 UIJIQXGRFSPYQW-UHFFFAOYSA-N 0.000 title claims description 4
- CNCZCYFROMADJV-UHFFFAOYSA-N purine-6-thione Chemical class S=C1N=CN=C2N=CN=C12 CNCZCYFROMADJV-UHFFFAOYSA-N 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- FDDCBLYAEALGPZ-UHFFFAOYSA-N 1,3-dimethyl-6-sulfanylidene-7h-purin-2-one Chemical compound S=C1N(C)C(=O)N(C)C2=C1NC=N2 FDDCBLYAEALGPZ-UHFFFAOYSA-N 0.000 claims description 4
- JZJPPRVXJHAHQM-UHFFFAOYSA-N 3-methyl-6-methylsulfanylpurine Chemical compound N1=CN(C)C2=NC=NC2=C1SC JZJPPRVXJHAHQM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical group ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000003212 purines Chemical class 0.000 description 6
- LUEYKVLQJDQJHM-UHFFFAOYSA-N 3-methyl-6-methylsulfanyl-8-phenylpurine Chemical compound CN1C=NC(=C2N=C(N=C12)C1=CC=CC=C1)SC LUEYKVLQJDQJHM-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- GERJKUSKMHORHI-UHFFFAOYSA-N CN1C=NC(=C2N=C(N=C12)C)SC Chemical compound CN1C=NC(=C2N=C(N=C12)C)SC GERJKUSKMHORHI-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229960000278 theophylline Drugs 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- AYDCZHIGNMCFPK-UHFFFAOYSA-N 3-methyl-7h-purine-6-thione Chemical class CN1C=NC(=S)C2=C1N=CN2 AYDCZHIGNMCFPK-UHFFFAOYSA-N 0.000 description 1
- RJOXFJDOUQJOMQ-UHFFFAOYSA-N 6-sulfanylidene-3,7-dihydropurin-2-one Chemical compound S=C1NC(=O)NC2=C1NC=N2 RJOXFJDOUQJOMQ-UHFFFAOYSA-N 0.000 description 1
- RNUXNXDOQICJRD-UHFFFAOYSA-N 8-phenyl-3,7-dihydropurin-6-one Chemical compound N1C=2C(=O)N=CNC=2N=C1C1=CC=CC=C1 RNUXNXDOQICJRD-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- -1 hydrosulphide ion Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-Butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UASZXGMETSWPKS-UHFFFAOYSA-N purine-2-thione Chemical compound S=C1N=CC2=NC=NC2=N1 UASZXGMETSWPKS-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 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
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Method for Preparation of 6-thioxo purines from 6-methylthio This invention relates to purine derivatives and more particularly to a novel method of preparing 3-methyl-6-thioxo-3,6-dihydro purines, and to certain novel purines derivatives so prepared.
These compounds are useful as growth inhibitors against bacterias and plant cells and as antitumor agents.
The conversion of alkylthio-3H-purines into the corresponding thioxo compounds is frequently an essential step in the synthesis of N-alkylated-6-thioxo-3,6-dihydro purines, and it is an object of the present invention to provide a method of demethylating the thio ether group of 3-methyl-6-methylthio-3H-purines and converting the latter to the corresponding 3-methyl-6-thioxo-7H-3,6-dihydro purines under very mild conditions.
According to the invention, a method of preparing a 3-methyl-6-thioxo-7H-3,6-dihydro purine comprises reacting the corresponding 3-methyl-6-(methyl-thio)-3H-purine with hydrogen sulphide in the presence of concentrated aqueous ammonia. The reaction can be carried out at room temperature, that is to say without the use of any external heating.
The method of the present invention can be applied to the preparation of the new compounds 3,8-dimethyl-6-thioxo-7H-3,6-dihydro purine: and 3-methyl-8-phenyl-6-thioxo-7H-3,6-dihydro-purine: CH3 from the corresponding 3,8-dimethyl-6-methylthio-3H-purine : and 3-methyl-8-phenyl-6-methylthio-3H-purine: which are themselves new compounds.
The novel starting materials may be conveniently prepared by reacting the corresponding 6-methylthio-3H-purine with methyl iodide in dirnethyljformamide in accordance with the method of Bergmann and Kleiner (Israel Journal of Chemistry, 1963, 1 , 477).
The method of the present invention can also (6-thiotheophylline) : from ^-dimethyl-^-methylthio-f-oxo-3H-t72-dihydro-purine: CH3 which is itself a new compound and which may be prepared by reacting 6-thioxo-theophylline with methyl iodide in aqueous caustic soda solution.
It is believed that the ease with which the demethylation is effected in the method of the present invention depends on the known fact that a 3-methyl group confers marked activity to the 6-position of purines. That this activity is not due to the fixation of a double bond in the 1 ,2-position but rather to the presence of a quinonoid imidazole-ring is shown by the fact that the corresponding ethers of 6-thioxanthine, such as the compound (VI) above, are readily converted into the corresponding thioxo-purine (V), and is confined by the fact that 6-methylthio purine itself does not react under the conditions of the present invention.
It is believed that the demethylation reaction of the present invention proceeds by splitting of the bond between the sulphur atom and the purine ring, the hydrosulphide ion performing a nucleophilic attack on carbon atom 6, thus releasing the 6-methylthio anion.
This invention is illustrated by the following examples Example 1. (a) Preparation of 3,8-dimethyl-6-methylthio-3H-purine (111) A suspension of S-methyl-e-thioxo^H-vl^-dihydro purine (22g), as described by Bergmann and Tamari (J. Chem. Soc. 1961 , p. 4468), in dry dimethylformamide (250 ml.) and freshly distilled methyl iodide (30 ml.) was refluxed for 2 hours. A further portion of methyl iodide ( 15 ml.) was then added and refluxing continued for a further 2 hours. The solvent was then removed in vacuo, the residue dissolved in water and an excess of concentrated ammonia was added to the acidic solution. Upon cooling, a white precipitate formed, which crystallised from acetonitrile in colourless needles (m.p. 195°C). Yield 12g. (47%).
Analysis: Calculated for C8 H i0 N 4S: C, 49.5 ; H, 5.2; N, 28.9 ; S, 16.5% Found: C, 49.4; H, 5.6 ; N, 28.8 ; S, 16.3% Preparation of 3,8-dimethyl-6-thioxo-7H-3,6-dihydro-purine (1) 3 ,8-D imethyl-6-me thy 1 thio-3 H-purine, prepared as above, (2 g.) was suspended in 25% aqueous ammonia (50 ml.) and hydrogen sulphide was bubbled through the suspension at room temperature for 20 minutes.
The reaction set in within a few minutes, as indicated by the rise in temperature and by dissolution of the suspended material. The final solution was brought to dryness in vacuo and the residue recrystallised from glacial acetic acid as sharp prisms, decomposing at 300°C. Yield 60%.
Analysis: Calculated for C 7H8 N4 S; C, 46.7; H, 4.4; N, 31.1 ; S, 17.8%.
Found: C, 46.7 ; H, 4.6; N, 30.8; S, 17.9%.
Example 2. (a) Preparation of 8-phenyl-6-thioxo-7 ej^H-Z^-dihydro purine A mixture of 8-phenylhypoxanthine (22g.), as described by Bergmann and Tamari (loc. ci ), phosphorus pentasulphide ( l OOg.) and dry 0-picoline (500ml.) was stirred and refluxed for 4 hours. The solvent was removed in vacuo and the residue treated with water (200ml.) at 70°C for 1 hour. The insoluble portion was triturated with 2N sodium hydroxide solution and the mixture passed through celite which retained the fine suspension of sulphur.
The solution was then decolourised with charcoal and acidified with acetic acid. The brown product was further purified by dissolving it in 5% sodium carbonate solution and treating the hot solution with charcoal. The sodium salt which crystallised on cooling was again dissolved in hot water and a hot, saturated solution of ammonium chloride was added. Light yellow needles were obtained, decomposing at above 300°C. Yield 19g. (80%).
Analysis: Calculated for CU H8 N4 S: C,57.9: H,3.5 ; N, 24.6%.
Found: C,57.2: H,3.6; N,24.2%. (b) Preparation of 3-methyl-8-phenyl-6-methylthio-3H-purine (IV) A solution of S-phenyl-e-thioxo-V^et-i^H-^^-dihydro-purine (39g.), prepared as described above, in dimethylformamide (600ml.) and freshly distilled methyl iodide (75ml.) was refluxed for 2 hours. A further portion of methyl iodide (40ml.) was then added and refluxing continued for a further 2 hours. The mixture, when cooled, precipitated a yellow product. The latter was dissolved in water and the pH adjusted to 10 by addition of 2N NaOH solution. The substance crystallised from isopropanol in while needles, m.p. 196-198°C. Yield 20g. (48%).
Analysis: Calculated for C13H 12 N4 S: C,60.9; H,4.7; N,12.9; S,12.5% Found: C.61 . 1 ; H,4.7; N.22. 1 ; S, 12.6%. (c) Preparation of 3-methyl-8-phenyl-6-thioxo-7H-3,6-dihydro-purine (II) 3-methyl-8-phenyl-6-methylthio-3H-purine (2g.) prepared as above, was dissolved in dimethylformamide ( 10ml.) and 0. 1 volumes of concentrated ammonia were added. Hydrogen sulphide was then bubbled through at room temperature for 20 minutes. The solution was brought to dryness in vacuo and the residue recrystallised from dilute acetic acid as yellow macrocrystalline aggregates, decomposing at 280-285°C. Yield 80% Analysis: Calculated for C12 H i0N4 S: C,59.5 ; H,4.1 ; N.23. 1 ; S, 13.2%.
Found: C, 59.5; H,4. 1 ; N.23.3 ; S, 13.5%.
Example 3.
Preparation of l S-dimethyl-e-metliylthio-^-oxo-SH-l^-dihydro-purine (VI) 6-Thiotheophylline (2.5g.), prepared as described by Woolridge and Slack (J. chem. Soc. 1962, p i 863), was dissolved in N NaOH solution ( 15 ml.) and the solution stirred with methyl iodide (2.5 ml.) at room temperature for 4 hours. After neutralization with acetic acid, the mixture was brought to dryness in vacuo.
The residue was extracted with isopropanol and the crude product recrystallised first from acetonitrile and then from isopropanol to form colourless needles of m.p. 189-191°C. Yield 0.6g. (22%).
Analysis: Calculated for C8 H I0N4 OS: C,45.7; H,4.8; N,26.7; S, 15.2%.
Found: C,45.8; H,5.0; N,26.2; S, 15.0%.
The new compound could be demethylated to 6-thiotheophylline by the process of the present invention as described in Example 1 with a yield of 80%.
The purity of the new compounds prepared in Example 1 to 3 was checked by measuring their molar extinction and by paper chromatography. The descending method was applied to Whatman No. 1 paper, using the following solvents: A - Ethanol: dimethylformamide: 25% ammonia . = 60:20:20 v/v B - Isopropanol: dimethylformamide: 25% ammonia = 65:25: 10: v/v C - n-Butanol: acetic acid: water = 60: 15:25 v/v Spots were located by their fluorescence under a Mineral light ultraviolet lamp, emitting light of about 255μ.
The physical constants so obtained are given in Tables I and II below.
TABLE I Physical constants of 3-methyl-6-methylthio-3H-purines m maaxx(mM) i ln solvent COMPOUND og„c emax RF *+ in Flue atPH8.0 A B C rmc 3,8-Dimethyl-6-methylthio-3 H 239 4.05 0.68 0.73 0.81 Green-yellow purine (III) 312 4.24 3-Methyl-6-methyl- 228 3.92 thio-8-phenyl-3H- 250 4.01 0.82 0.76 Blue purine (IV) 337 4.28 351 4.22 ls3,-Dimethyl-6-methylthio-J-oxo- 257 3.84 0.69 0.83 Blue-violet 3H-*S-dihydro-purine (VI) 334 4.11 All RF values refer to theophylline (Rp = 0.68 in all solvents) as standard.
TABLE II Physical constants of 3-methyl-6-thioxo-7H-3,6-dihydro purines (τημ) 'Vnax Rp + in solvent COMPOUND log emax Fluorescence at pH 8.0 A B C 3,8-Dimethyl-6-thioxo-7H- 3,6-dihydro purine 248 3.94 0.68 0.56 0.56 Yellow-green (I) 336 4.33 3-Methyl-8-phenyl-6-thioxo- 7H-3,6-dihydro-purine 261 4.31 0.75 0.68 Yellow (HI) 361 4.57 + All RF values refer to theophylline (RF = 0.68 in all solvents) as standard.
Claims (4)
1. WE CLAIM: A method of preparing a 3-methyl-6-thioxo-7H-3,6- dihydro-purine which comprises reacting the corresponding 3-methyl-6-methylthio-3H-purine with hydrogen sulphide in the presence of concentrated aqueous ammonia.
2. A method according to Claim 1, wherein the reaction is carried out without external heating.
3. A method according to claims 1 and 2 for the preparation of 3-methyl-6-thioxo-7H-3,6-dihydro-purine of the general formula: where R is a methyl group or a phenyl group which comprises reacting a compound of the formula: where R is as defined above, with hydrogen sulphide in presence of concentrated aqueous ammonia.
4. A method according to Claim 3, wherein the 3-methyl- 6-methylthio-¾H 3;6 dihydre purine is prepared by reacting the corresponding 6-methylthio-3H-purine with methyl iodide in dimethylformamide. A method according to claims 1 and 2 for preparing 6-thiotheophylline of the formula: k which comprises reacting a compound of the formula: with hydrogen sulphide in the presence of concentrated aqueous ammonia. A method of preparing 3-methyl-6-thioxo-7H-3,6-dihydro- purines substantially as hereinbefore described with reference to Example 1. New compounds of the general formula: where R is methyl or phenyl 3 , 8-D imethy 1-6- thioxo-7H-3 , 6-dihy dro-purine 3-Methyl-8-phenyl-6-thioxo-7H-3,6-dihydro-purine 10. 3,5-Dimethyl-6-methylthio-4-oxo-3H-4,5-dihydro-purine
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2464265A IL24642A (en) | 1965-11-18 | 1965-11-18 | Method for preparation of 6-thioxo purines from 6-methylthio purines |
| GB5541265A GB1073039A (en) | 1965-11-18 | 1965-12-31 | Improvements in or relating to purine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2464265A IL24642A (en) | 1965-11-18 | 1965-11-18 | Method for preparation of 6-thioxo purines from 6-methylthio purines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24642A true IL24642A (en) | 1971-06-23 |
Family
ID=11043761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2464265A IL24642A (en) | 1965-11-18 | 1965-11-18 | Method for preparation of 6-thioxo purines from 6-methylthio purines |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1073039A (en) |
| IL (1) | IL24642A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| EP1202628B1 (en) * | 1999-08-12 | 2004-10-13 | Euro-Celtique S.A. | Novel hypoxanthine and thiohypoxanthine compounds |
| RU2233842C1 (en) * | 2003-01-13 | 2004-08-10 | Петров Владимир Иванович | Derivatives of purine eliciting antiviral activity |
-
1965
- 1965-11-18 IL IL2464265A patent/IL24642A/en unknown
- 1965-12-31 GB GB5541265A patent/GB1073039A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1073039A (en) | 1967-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Paull et al. | The synthesis of XTT: A new tetrazolium reagent that is bioreducible to a water‐soluble formazan | |
| Sykes et al. | 113. Aneurin. Part X. The mechanism of thiochrome formation from aneurin and aneurin disulphide | |
| SE7712060L (en) | PROCEDURE FOR THE PREPARATION OF FUROCUMARINES | |
| US3856777A (en) | Method of producing pyrimidine nucleoside derivatives | |
| Yamazaki et al. | Synthesis of guanosine and its derivatives from 5-amino-1-. beta.-D-ribofuranosyl-4-imidazolecarboxamide. II. Ring closure with sodium methyl xanthate | |
| IL24642A (en) | Method for preparation of 6-thioxo purines from 6-methylthio purines | |
| US2697709A (en) | Mercapto heterocycles and method of making | |
| Cook et al. | 50. Studies in the azole series. Part III. The interaction of aminoacetonitrile and carbon disulphide | |
| NO131106B (en) | ||
| HU182010B (en) | Novel 2,2-dimethyl-1,2-dihydro-quinoline derivatives having anti-oxidant activity | |
| Baker et al. | Synthesis of derivatives of thiazolo [4, 5-d] pyrimidine. Part I | |
| US2721866A (en) | Process of manufacture of 6-mercapto purine and intermediate therefor | |
| SU649710A1 (en) | Method of obtaining 4,4'-bis-(4''-chlorphenylthio)-diphenylsumfone | |
| KR910006983B1 (en) | Process for the preparation of pyridine derivatives | |
| US3132144A (en) | Z-amevo-g-iodopurine | |
| US3359290A (en) | Production of omega-aminoketo-carboxylic acids | |
| SU436493A3 (en) | ||
| SU767098A1 (en) | Method of preparing potassium 1,2,6,6-tetramethylpiperidine-1-oxyl-4-xanthogenate | |
| US3654292A (en) | Manufacture of 3 5-dichloro-2 6-difluoro - 4 - hydroxypyridine and salts thereof | |
| US3260755A (en) | Preparation of aromatic disulfides | |
| US3357976A (en) | Mercury derivatives of certain as-triazine-5 (2h)-ones | |
| Shealy et al. | Acidic Cleavage of Amino [1, 2, 5] thiadiazolo [3, 4-d]-and-v-triazolo [4, 5-d] pyrimidines to 1, 2, 5-Thiadiazole-1 and v-Triazolecarboxamidines2 | |
| Cook et al. | 209. Studies in the azole series. Part IV. The preparation of some thiazolones | |
| KR910009816B1 (en) | Process for preparing of pyridine derivated | |
| US3318897A (en) | Novel method for preparing yohimbinone |