26944-48-9

Basic information

• Product Name: Glibornuride
• Synonyms: Glibornuride;1-[p-Tolylsulfonyl]-3-[2-endo-hydroxy-3-endo-D-bornyl] urea;Glitrim;N-[[[(1S,2S,3R,4R)-2-Hydroxyborn-3-yl]amino]carbonyl]-4-methylbenzenesulfonamide;Ro-6-4563;1-(3-hydroxy-4,7,7-trimethyl-norbornan-2-yl)-3-(4-methylphenyl)sulfonyl-urea;1-(6-hydroxy-1,7,7-trimethyl-5-bicyclo[2.2.1]heptanyl)-3-(4-methylphenyl)sulfonylurea;1-(6-hydroxy-1,7,7-trimethyl-5-bicyclo[2.2.1]heptanyl)-3-(4-methylphenyl)sulfonyl-urea
• CAS NO: 26944-48-9
• Molecular Formula: C₁₈H₂₆N₂O₄S
• Molecular Weight: 366.47504
• EINECS: 248-124-6
• Product Categories: Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 26944-48-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 192-195° (ethanol-water); also reported as 195-198°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.1793 (rough estimate)
• Refractive Index: 1.6930 (estimate)
• PKA: 5.20±0.10(Predicted)
• CAS DataBase Reference: Glibornuride(CAS DataBase Reference)
• NIST Chemistry Reference: Glibornuride(26944-48-9)
• EPA Substance Registry System: Glibornuride(26944-48-9)

Safety Data

• Hazardous Substances Data: 26944-48-9(Hazardous Substances Data)

Usage

Originator

Glutril,Roche,W. Germany,1972

Uses

Glibornuride has been shown to antagonize the relaxant response to the K+ channel opener cromakalim and produce airway smooth muscle relaxation. Glibornuride is associated with lactic acidosis and hypoglycemia in patients with type 2 diabetes melitus.

Manufacturing Process

2.1 grams of 3-endo-aminoborneol hydrochloride and 2.4 grams of O-methylN-p-toluene-sulfonyl-urea are heated at 125°C for 3 hours with 2 ml of dimethylformamide. After cooling, the reaction mixture is stirred with 100 ml of water for 10 minutes, while a pH of 3.5 is maintained by the addition of a few drops of dilute hydrochloric acid. The precipitate is removed by filtration, washed with water and suspended in 100 ml of water. The suspension is dissolved by the addition of 20 ml of 1 N caustic soda. The alkaline solution is extracted with ether, acidified with dilute hydrochloric acid and filtered. The precipitate is washed with water and recrystallized from alcohol/water to yield 1-(p-toluene-sulfonyl)-3-(2-endo-hydroxy-3-endo-bornyl)-urea having a melting point of 193° to 195°C.

Brand name

Glutril (Hoffmann-LaRoche).

Therapeutic Function

Oral hypoglycemic

InChI:InChI=1/C18H26N2O4S/c1-11-5-7-12(8-6-11)25(23,24)20-16(22)19-14-13-9-10-18(4,15(14)21)17(13,2)3/h5-8,13-15,21H,9-10H2,1-4H3,(H2,19,20,22)

Downstream Products

• 70-55-3 toluene-4-sulfonamide 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 103-19-5 di(p-tolyl) disulfide 
• 80-48-8 methyl p-toluene sulfonate 
• 108-88-3 toluene 
• 1888-33-1 N-acetyl-(4-methylbenzene)sulfonamide 
• 41719-63-5 (1R,2R,6S,7S)-(-)-1,10,10-trimethyl-3-oxa-5-azatricyclo[5.2.1.0(2,6)]decan-4-one 
• 41719-61-3 (toluene-4-sulfonyl)-((4S)-7,8,8-trimethyl-(3ac,7ac)-3a,4,5,6,7,7a-hexahydro-4r,7c-methano-benzooxazol-2-yl)-carbamic acid ethyl ester 

Relevant articles and documents

USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS

The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula