Octreotide pamoate → Pamoic Acid

HRID 1395928Notes

Reaction equation

HRID 1395928 reaction equation
C[C@@H](O)[C@@H]1NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC2C3C=CC=CC=3NC=2)NC(=O)[C@H](CC2C=CC=CC=2)NC(=O)[C@@H](NC([C@H](N)CC2C=CC=CC=2)=O)CSSC[C@@H](C(N[C@@H]([C@H](O)C)CO)=O)NC1=O.[CH:72]1[CH:73]=[CH:74][C:75]2[C:76](=[CH:78][C:79]([C:98]([OH:100])=[O:99])=[C:80]([OH:97])[C:81]=2[CH2:82][C:83]2[C:92]([OH:93])=[C:91]([C:94]([OH:96])=[O:95])[CH:90]=[C:89]3[C:84]=2[CH:85]=[CH:86][CH:87]=[CH:88]3)[CH:77]=1>CCOC(C)=O.C(O)C1C=CC=CC=1>[CH:72]1[CH:73]=[CH:74][C:75]2[C:76](=[CH:78][C:79]([C:98]([OH:100])=[O:99])=[C:80]([OH:97])[C:81]=2[CH2:82][C:83]2[C:92]([OH:93])=[C:91]([C:94]([OH:96])=[O:95])[CH:90]=[C:89]3[C:84]=2[CH:85]=[CH:86][CH:87]=[CH:88]3)[CH:77]=1

Participants

4

Reactant 1

HCID 44194024Octreotide pamoate

Product 1

HCID 8546Pamoic Acid

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 8857Ethyl AcetateSolvent

Procedure

Microparticle formulations (Table 5, Q-W) were prepared by an oil-in-water emulsion/solvent extraction method. PLGA polymer (MW 24,000, 180 mg) was dissolved in EtOAc (1000 μL). Octreotide pamoate (20 or 40 mg) was dissolved in benzyl alcohol (BnOH, 1000 μL) and added to the polymer solution yielding a homogeneous organic phase. The resulting organic phase was combined with a 1% PVA aqueous phase in a ratio of 1:2 to provide an emulsion. The emulsion was collected directly into a 0.3% PVA solvent extraction solution (150 mL) and stirred for four hours to extract EtOAc. Hardened microparticles were collected by filtration, washed with water, air dried and stored at 4° C.

Workup

  1. additionadded to the polymer solution
  2. customyielding a homogeneous organic phase
  3. customto provide an emulsion
  4. customThe emulsion was collected directly into a 0.3% PVA solvent extraction solution (150 mL)
  5. extractionto extract EtOAc
  6. filtrationHardened microparticles were collected by filtration
  7. washwashed with water, air
  8. customdried
  9. customstored at 4° C.

Sources & evidence

ORD record
ord-362ac787d9b2419e8b184b5e68b65f9f
Source dataset
uspto-grants-2014_12
Patent number
US08900636B2

Reaction notes

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