← Back to Patent Explorer
US3681394A Expired / Lapsed US ⏱️ 0.0 years remaining

Glyceryl-n-(substituted phenyl) anthranilates

Assignee: Merck Sharp & Dohme LLC
•
Filing: 1970-01-21
•
Granted: 1972-08-01
•
Expires: 1990-01-21
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The invention relates to glyceryl esters of N-X,Y,Z-phenyl (anthranilic acids), to their use as analgesic anti-inflammatory agents, and to the intermediates useful in the preparation thereof. Illustrative of the preparation of those compounds is the formation of glyceryl-N-(3-trifluoromethylphenyl) anthranilate, as follows: Reflux a mixture containing N-(3trifluoromethylphenyl) anthranilic acid, chloroacetonitrile in the presence of triethylamine to produce cyanomethyl-N-(3trifluoromethylphenyl) anthranilate which, by heating with 2,2dimethyl-1,3-dioxolane-4-methanol in the presence of anhydrous potassium carbonate, produces Beta - gamma isopropylidenedioxypropyl anthranilate. Hydrolysis of the Beta gamma -isopropylidenedioxypropyl-N-(3-trifluoromethylphenyl) anthranilate with 75 percent acetic acid for 35 minutes yields glyceryl N-(3-trifluoromethylphenyl) anthranilate. Alternate methods for the preparation of the glyceryl esters of N-(X,Y,Zphenyl) anthranilic acids are also described.

Inventors

  • 👤 Margaret H Sherlock

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 16:13
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; C07C; C07C255/00; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/24

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 15 words
A compound of claim 1 wherein Y and Z are hydrogen and X is trifluoromethyl.
Claim 2
Dependent Claim 16 words
A compound of claim 1 wherein Y is hydrogen, X is methyl and Z is chloro.
Claim 3
Dependent Claim 16 words
A compound of claim 1 wherein Y is hydrogen, X is methyl and Z is nitro.
Claim 4
Dependent Claim 22 words
A compound of claim 1 wherein Y and Z are hydrogen, X is trifluoromethyl, said compound being Beta , gamma -isopropylidenedioxypropyl-N-(3-trifluoromethylphenyl) anThranilate.
Claim 5
Dependent Claim 23 words
A compound of claim 1 wherein Y is hydrogen, X is methyl, Z is chloro, said compound being Beta , gamma -isopropylidenedioxypropyl-N-(2-methyl-3-chlorophenyl) anthranilate.
Claim 6
Dependent Claim 23 words
A compound of claim 1 wherein Y is hydrogen, X is methyl, Z is nitro, said compound being Beta , gamma -isopropylidenedioxypropyl-N-(2-methyl-3-nitrophenyl) anthranilate.

References Cited (Backward Citations)

US3390172A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1975-08-01 1976-01-31 1976-08-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1979-08-01 1980-01-31 1980-08-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1983-08-01 1984-01-31 1984-08-01 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag