Glimepiride(glimepiride)Il nome chimico è1-[4-[2-(3-etil-4-metil-2-Osso-3-pirroline-1-gruppo di formamide)-etil]-Benzenesulfonil]-3-(Trans-4-metil cicloesil)-urea, polvere cristallina bianca, inodore, insapore. Scioglito in cloroformio, molto leggermente solubile in metanolo o etanolo, insolubile in acqua o etere. La formula molecolare è C24H34N4O5S, il peso molecolare è 490.61600, la densità è 1,29 g/cm3, il punto di fusione è 212,2-214,5°C.
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Massa esatta: 490.6g/mol
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Carica superficiale: 0
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XLogP3: 3.9
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Conta donatori di obbligazioni idrogeno: 3
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Conta accettatore di obbligazioni idrogeno: 5
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Conta legami ruotabili: 7
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Massa monoisotopica: 490.224991g/mol
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Massa monoisotopica: 490.224991g/mol
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Superficie polare topologica: 133Ų
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Conta atomi pesanti: 34
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Complessità: 895
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Conta atomi isotopi: 0
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Conto di stereocentri atomici definito: 0
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Conta stereocentri atomici non definiti: 0
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Conto stereocentrico definito delle obbligazioni: 0
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Conto stereocenter di bond non definito: 0
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Conteggio di unità legate in modo Covalent: 1
- Conta Tautomer: 6
- Carica superficiale: 0
Circuito sintetico 1
1.1
Solvents:
tert-Butyl methyl ether
1.2
Solvents:
Toluene
,
Cyclohexanone
,
tert-Butyl methyl ether
;
10 h, 30 °C
Riferimento
Method for preparing hypoglycemic drug glimepiride
,
China,
,
,
Circuito sintetico 2
1.1
Solvents:
Toluene
;
rt
1.2
rt → reflux; 4 h, reflux; reflux → 15 °C
Riferimento
Process for preparing glimepiride and corresponding intermediate
,
Czech Republic,
,
,
Circuito sintetico 3
1.1
Reagents:
Potassium carbonate
Solvents:
Tetrahydrofuran
;
1 - 2 h, rt → 65 °C
1.2
Solvents:
Toluene
;
10 - 12 h, 60 - 65 °C; cooled
1.3
Reagents:
Ammonia
Solvents:
Methanol
;
pH 10 - 12
1.4
Reagents:
Acetic acid
;
pH 5.5 - 6.0, 25 - 30 °C
Riferimento
A process for purification of glimepiride
,
India,
,
,
Circuito sintetico 4
Riferimento
Studies on synthetic process of glimepiride, new hypoglycemic agent
Deng, Yong;
Zhong, Yuguo;
Tang, Weigao;
Zhong, Zhicheng,
Zhongguo Yaowu Huaxue Zazhi,
2000,
10(2),
134-137
Circuito sintetico 5
1.1
Reagents:
Triethylamine
,
Ethyl chloroformate
Solvents:
Dichloromethane
;
2 h, 20 - 25 °C
1.2
Reagents:
Acetic acid
Solvents:
Water
;
pH 4 - 4.2; 30 min
1.3
Reagents:
4-(Dimethylamino)pyridine
Solvents:
Toluene
;
rt → reflux; 3 h, reflux; reflux → 30 °C; 3 h, 25 - 30 °C
Riferimento
An improved process for the preparation of N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide, a key intermediate in the synthesis of glimepiride
,
India,
,
,
Circuito sintetico 6
1.1
Reagents:
Sodium hydroxide
,
Zinc chloride
Solvents:
Dimethylformamide
,
Water
;
pH 6.5 - 8, rt; 3 h, 80 °C
Riferimento
Synthesis, physico-chemical and antidiabetic studies of zinc complex of glimepiride, an oral hypoglycemic agent
Jacob, George,
Oriental Journal of Chemistry,
2013,
29(4),
1351-1358
Circuito sintetico 7
1.1
Reagents:
4-(Dimethylamino)pyridine
Solvents:
Toluene
;
rt → reflux
Riferimento
Method for the manufacture of compounds related to the class of substituted sulfonyl urea antidiabetics
,
European Patent Organization,
,
,
Circuito sintetico 8
1.1
Reagents:
Potassium carbonate
Solvents:
Acetone
,
Methyl ethyl ketone
;
30 min, rt → reflux
1.2
5 - 6 h, reflux
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
pH 6
Riferimento
Preparation of glimepiride
,
China,
,
,
Circuito sintetico 9
1.1
Reagents:
Potassium carbonate
Solvents:
Acetone
;
6 h, reflux
1.2
6 h, reflux; reflux → rt
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
pH 2
Riferimento
studies on the preparation of glimepiride
Liu, Sheng-gao,
Shandong Huagong,
2009,
38(6),
14-15
Circuito sintetico 10
1.1
Reagents:
Diisopropylethylamine
Solvents:
Dimethylformamide
;
3 h, rt → 25 °C
1.2
Solvents:
Dimethylformamide
;
overnight, heated
Riferimento
Preparation method of glimepiride
,
China,
,
,
Circuito sintetico 11
1.1
Reagents:
Triethylamine
Solvents:
Dichloromethane
;
7 h, rt
Riferimento
Preparation method of glimepiride for anti-diabetes drug
,
China,
,
,
Circuito sintetico 12
1.1
Reagents:
Sodium methoxide
Solvents:
Dimethyl sulfoxide
1.2
Reagents:
Water
Riferimento
Improved process for the preparation of benzenesulfonylureas used as second-generation oral hypoglycemic agents
,
World Intellectual Property Organization,
,
,
Circuito sintetico 13
1.1
Reagents:
Potassium carbonate
Solvents:
Acetone
;
1 h, 55 - 60 °C
1.2
Solvents:
Toluene
;
12 h, reflux
1.3
Reagents:
Acetic acid
Solvents:
Water
;
pH 5.5 - 6, 20 - 25 °C
Riferimento
A novel process for preparation of substantially pure glimepiride
,
World Intellectual Property Organization,
,
,
Circuito sintetico 14
1.1
Reagents:
1,8-Diazabicyclo[5.4.0]undec-7-ene
Solvents:
Acetonitrile
;
5 h, reflux
Riferimento
An Efficient and Practical Process for the Synthesis of Glimepiride
Tanwar, Dinesh Kumar;
Surendrabhai, Vaghela Ravikumar;
Gill, Manjinder Singh,
Synlett,
2017,
28(18),
2495-2498
Circuito sintetico 15
1.1
Reagents:
Potassium carbonate
Solvents:
Acetonitrile
;
rt → 60 °C
1.2
6 h, 50 - 60 °C
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
pH 1 - 2, 20 - 25 °C
Riferimento
Synthetic preparation of glimepiride bulk drug
,
China,
,
,
Circuito sintetico 16
1.1
Reagents:
Potassium carbonate
Solvents:
Acetone
;
6 h, reflux
1.2
8 h, reflux; reflux → rt
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
pH 1 - 2
Riferimento
Synthesis of 3-ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide (glimepiride)
Liu, Zhanke;
Yang, Xinwu;
Lu, Qihui;
Wang, Xiaoguang;
Liu, Zhiling,
Jingxi Huagong Zhongjianti,
2006,
36(3),
16-18