Reaction #2467925

ord-9ec321def3f54e1883322b4f7ae5545b

Reaction equation

CC1(C)O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
Triamcinolone acetonide
C[C@]12C=CC(=O)C=C1[C@@H](F)C[C@H]1[C@@H]3C[C@@H](O)[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@]12F
fluocinolone
→
C[C@]12C=CC(=O)C=C1CC[C@H]1[C@@H]3C[C@@H](O)[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@]12F
Triamcinolone

Reactants

—
steel
CC1(C)O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
Triamcinolone acetonide
—
stainless steel
C[C@]12C=CC(=O)C=C1[C@@H](F)C[C@H]1[C@@H]3C[C@@H](O)[C@](O)(C(=O)CO)[C@@]3(C)C[C@H](O)[C@@]12F
fluocinolone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONmixed
  2. 2
    workup.ADDITIONmixed again for an additional 15 minutes
  3. 3
    TemperatureThe powder blend was heated at temperatures
  4. 4
    Otherranging from 110° C. to 160° C.
  5. 5
    Otherused, for a total of 30 minutes
  6. 6
    Otherforming a polymer/drug

Procedure

Triamcinolone acetonide was combined with a polymer in a stainless steel mortar and mixed using the Turbula shaker set at 96 RPM for 15 minutes. The powder of the fluocinolone and polymer was scraped off the walls of the steel mortar and then mixed again for an additional 15 minutes. The powder blend was heated at temperatures ranging from 110° C. to 160° C., depending on the polymer used, for a total of 30 minutes, forming a polymer/drug melt. The melt was pelletized, then loaded into the barrel and extruded into filaments, and finally the filaments were cut into about 0.5 mg or about 1 mg size implants. The implants had a weight range from about 450 μg to about 550 μg, or from about 900 μg to about 1100 μg. The 1 mg size implants had a length of about 2 mm and a diameter of about 0.72 mm.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08257730B2uspto-grants-2012_09