1. chem960
  2. 93479-97-1
Glimepiride | 93479-97-1

Product name:Glimepiride

CAS No:93479-97-1
MF:C24H34N4O5S
MW:490.615564823151
MDL:MFCD00878417
CID:61633
PubChem ID:160870906
Introduction
        Glimepiride(glimepiride)The chemical name is1-[4-[2-(3-ethyl-4-methyl-2-Oxo-3-Pyrroline-1-Formamide group)-ethyl]-Benzenesulfonyl]-3-(Trans-4-Methyl cyclohexyl)-urea,White crystalline powder,Odorless,tasteless.Dissolved in chloroform,Very slightly soluble in methanol or ethanol,Insoluble in water or ether.The molecular formula isC24H34N4O5S,The molecular weight is490.61600,The density is1.29 g/cm3,Melting point is212.2-214.5°C.

Names and Identifiers
  • Glimepiride
  • glimepirid
  • hoe490
  • 1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea
  • amary
  • AMARYL
  • Glimperide
  • CLIMEPIRIDE
  • GliMepiride COS
  • Glimpiride
  • Grimepride
  • trans-3-Ethyl-2,5-dihydro-4-methyl-N-[N-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide
  • HOE-490
  • Glimepiride impurity
  • Amarel
  • Glimepiridum
  • Glimepirida
  • Endial
  • Glimepride
  • cis-Glimepiride
  • Glimepiridum [Latin]
  • HOE 490
  • Glimepirida [Spanish]
  • Glista OD
  • 4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide
  • 1-((p-(2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl)phenyl)sulfonyl)-3-(trans-4-methylcyclohexyl)urea
  • 24T6XIR2MZ
  • 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-, trans- (ZCI)
  • 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 (ACI)
  • Amaryl
  • Diameprid
  • Dibiglim
  • Glimax
  • Glirid
  • GlucoNovax
  • Limeral
  • trans-3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl] 2-oxo-1H-pyrrole-1-carboxamide
  • ZINC 537791
  • MDL:MFCD00878417
  • InChIKey:WIGIZIANZCJQQY-RUCARUNLSA-N
  • Inchi:1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19-
  • SMILES:C(N1CC(C)=C(CC)C1=O)(=O)NCCC1C=CC(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)=CC=1
  • BRN:5365754
Chemical and Physical Properties

Computed Properties

  • Exact Mass: 490.6g/mol
  • Surface Charge: 0
  • XLogP3: 3.9
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Rotatable Bond Count: 7
  • Monoisotopic Mass: 490.224991g/mol
  • Monoisotopic Mass: 490.224991g/mol
  • Topological Polar Surface Area: 133Ų
  • Heavy Atom Count: 34
  • Complexity: 895
  • Isotope Atom Count: 0
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Covalently-Bonded Unit Count: 1
  • Tautomer Count: 6
  • Surface Charge: 0

Experimental Properties

  • LogP: 5.26540
  • PSA: 133.06000
  • Merck: 4440
  • Refractive Index: 1.599
  • Boiling Point: No data available
  • Melting Point: 202.0 to 206.0 deg-C
  • Flash Point: No data available
  • Color/Form: Powder
  • Solubility: Not determined
  • Density: 1.29
Security Information
  • Symbol: GHS08
  • RTECS:UX9363950
  • WGK Germany:3
  • Safety Instruction:S25-S26-S36/37-S53
  • Risk Phrases:R21
  • खतरनाक माल साइन: Xn Xn Xi Xi
  • Hazardous Material transportation number:NONH for all modes of transport
  • Hazard Statement:H361
  • Warning Statement:P280
  • Prompt:warning
  • Storage Condition:Powder -20°C 3 years   4°C 2 years In solvent -80°C 6 months   -20°C 1 month
  • Hazard Category Code:R21: harmful in contact with skin. R46: may cause genetic damage. R62: risk of weakening reproductive capacity. R63: may harm unborn infants. R36/38: irritating to eyes and skin.
  • Signal Word:Warning
Customs Data
  • HS CODE:2935009090
  • Customs Data:

    China Customs Code:

    2935009090

    Overview:

    2935009090 Other sulphonates(Acyl)amine. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:35.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Synthetic Circuit

Synthetic Circuit 1

Reaction Conditions
1.1 Solvents: tert-Butyl methyl ether
1.2 Solvents: Toluene ,  Cyclohexanone ,  tert-Butyl methyl ether ;  10 h, 30 °C
Reference
Method for preparing hypoglycemic drug glimepiride
, China, , ,

Synthetic Circuit 2

Reaction Conditions
1.1 Solvents: Toluene ;  rt
1.2 rt → reflux; 4 h, reflux; reflux → 15 °C
Reference
Process for preparing glimepiride and corresponding intermediate
, Czech Republic, , ,

Synthetic Circuit 3

Reaction Conditions
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
Reference
A process for purification of glimepiride
, India, , ,

Synthetic Circuit 4

Reaction Conditions
1.1 Solvents: Toluene
Reference
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

Synthetic Circuit 5

Reaction Conditions
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
Reference
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, , ,

Synthetic Circuit 6

Reaction Conditions
1.1 Reagents: Sodium hydroxide ,  Zinc chloride Solvents: Dimethylformamide ,  Water ;  pH 6.5 - 8, rt; 3 h, 80 °C
Reference
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

Synthetic Circuit 7

Reaction Conditions
1.1 Reagents: 4-(Dimethylamino)pyridine Solvents: Toluene ;  rt → reflux
Reference
Method for the manufacture of compounds related to the class of substituted sulfonyl urea antidiabetics
, European Patent Organization, , ,

Synthetic Circuit 8

Reaction Conditions
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
Reference
Preparation of glimepiride
, China, , ,

Synthetic Circuit 9

Reaction Conditions
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
Reference
studies on the preparation of glimepiride
Liu, Sheng-gao, Shandong Huagong, 2009, 38(6), 14-15

Synthetic Circuit 10

Reaction Conditions
1.1 Reagents: Diisopropylethylamine Solvents: Dimethylformamide ;  3 h, rt → 25 °C
1.2 Solvents: Dimethylformamide ;  overnight, heated
Reference
Preparation method of glimepiride
, China, , ,

Synthetic Circuit 11

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  7 h, rt
Reference
Preparation method of glimepiride for anti-diabetes drug
, China, , ,

Synthetic Circuit 12

Reaction Conditions
1.1 Reagents: Sodium methoxide Solvents: Dimethyl sulfoxide
1.2 Reagents: Water
Reference
Improved process for the preparation of benzenesulfonylureas used as second-generation oral hypoglycemic agents
, World Intellectual Property Organization, , ,

Synthetic Circuit 13

Reaction Conditions
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
Reference
A novel process for preparation of substantially pure glimepiride
, World Intellectual Property Organization, , ,

Synthetic Circuit 14

Reaction Conditions
1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Acetonitrile ;  5 h, reflux
Reference
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

Synthetic Circuit 15

Reaction Conditions
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
Reference
Synthetic preparation of glimepiride bulk drug
, China, , ,

Synthetic Circuit 16

Reaction Conditions
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
Reference
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
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G0395-1G >98.0%(T)(HPLC) 上海:6/天津:5/日本:≥40 1g ¥505.00 08 Sep. 2023
G0395-5G >98.0%(T)(HPLC) 上海:2/天津:11/日本:23 5g ¥1575.00 08 Sep. 2023
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