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Thymine nucleobase-based triazolopyrimidines and production method therefor

A manufacturing method and a technology for triazololation, which can be used in the field of antitumor agents and can solve problems such as strong side effects

Pending Publication Date: 2021-11-23
TERA STONE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned existing drugs and their metabolites inhibit (metabolically antagonize) the synthesis of nucleic acids and show anti-tumor effects, but strong side effects are predicted, and therefore, in the judgment of doctors familiar with the treatment using the above-mentioned drugs under treatment

Method used

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  • Thymine nucleobase-based triazolopyrimidines and production method therefor
  • Thymine nucleobase-based triazolopyrimidines and production method therefor
  • Thymine nucleobase-based triazolopyrimidines and production method therefor

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0166] [Example 1.3-substituted 8-methyl-[1,2,4]triazolo[4,3- c ]pyrimidine-5(6 H )-keto compound 4a-f, s, t (general formula I) and 2-substituted 8-methyl-[1,2,4]triazolo[1,5- c ]pyrimidine-5(6 H )-Kone compound 5a-t (general formula II) synthesis example]

[0167] Triazolopyrimidine compounds represented by compounds 4a-f, s, t and 5a-t were synthesized according to the reaction formula described in Scheme 1 above.

Synthetic example 1

[0169] 4-hydrazino-5-methylpyrimidine-2(1 H )-Synthesis of ketone compound 2

[0170] Add 4-thiothymine compound 1 (1 g, 7.0 mmol) and hydrazine hydrate (2 g, 40 mmol) to EtOH (8 mL), and heat to reflux for 10 minutes. After the reaction, the precipitated crystals were collected by filtration. It was recrystallized from water to give colorless needles (0.80 g, 81%, mp>300°C).

[0171] [chemical formula 15]

[0172] 1 H NMR [200MHz, (CD 3 ) 2 SO]δ: 1.68 (3H, s, 5-Me), 5.82 (2H, br s, interchangeable with D20, NH 2 ), 6.68 (1H, br s, interchangeable with D20, 6-H), 9.41 (2H, br, interchangeable with D20, NH); IR: 3260 (ν as , NH 2 ), 3180(ν s , NH 2 ), 3130, 3060 (ν, NH), 1660 (ν, C=O), 1600cm -1 (δ, NH 2 ); analysis and calculation value C 5 h 8 N 4 O·1 / 2H 2 O: C, 40.26; H, 6.08; N, 37.56 Experimental value: C, 39.97; H, 5.96; N, 37.73; MS (FAB, glycerol matrix): m / z=141 (MH + ).

Synthetic example 2

[0174] 4-Alkylidenehydrazino-5-methylpyrimidine-2(1 H )-ketone and 4-arylmethylidenehydrazino-5-methylpyrimidine-2(1 H General Synthesis of )-Kone Compounds 3a-r

[0175] To MeOH (25 mL) was added 4-hydrazino-5-methylpyrimidine-2 (1 H )-ketone compound 2 (4mmol) and various aldehydes (4.8mmol), stirred at room temperature for 30 minutes to 2 hours. After the reaction, the precipitated crystals were collected by filtration and recrystallized from EtOH to obtain the corresponding target compounds 3a-r (Tables 1-4).

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Abstract

Provided are: novel triazolopyrimidines that can be induced from the nucleobase thymine; a production method for the triazolopyrimidines; and various physiologically active substances, particularly an antitumor agent, obtained by the method. These triazolopyrimidine compounds are represented by formulas (I)-(VIII) (in the formulas, R represents a hydrogen atom, an alkyl group, or an aryl group). This production method produces the triazolopyrimidine compounds.

Description

technical field [0001] The present invention relates to a novel triazolopyrimidine compound which can be derived from nucleic acid base thymine or uracil, its production method, and various physiologically active substances obtained by the method, especially antitumor agents. Background technique [0002] Heidelberger et al established the evaluation of fluorouracil (5-fluorouracil, 5-FU) as an anti-malignant tumor agent through extensive basic and clinical research. It has a structure in which the 5-position hydrogen atom of uracil is replaced by a fluorine atom. Since the 1990s, improvements such as prodrugization of fluorouracil have been carried out, and drugs (internal medicines) that are expected to have higher effects have been developed and marketed. It is used to relieve the subjective and objective symptoms of gastric cancer, liver cancer, colorectal cancer, breast cancer, pancreatic cancer, cervical cancer, uterine body cancer and ovarian cancer. In addition, it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P35/00C07D487/04A61K31/519
CPCC07D487/04A61P35/00A61K31/519
Inventor 永松朝文
Owner TERA STONE CO LTD
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