4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid → (+)-Niguldipine

HRID 1003920Notes

Reaction equation

HRID 1003920 reaction equation
[CH3:1][C:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[O:10])[C@H:4]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[CH:34]=2)[C:3]=1[C:42]([O:44][CH3:45])=[O:43].Cl.C1N(CCO)CCN(CCS(O)(=O)=O)C1.CC(N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O)=O.CCC(C([O-])=O)CC(C([O-])=O)CC(C([O-])=O)CC(C([O-])=O)C.[Na+].[Na+].[Na+].[Na+]>CS(C)=O>[CH3:1][C:2]1[NH:7][C:6]([CH3:8])=[C:5]([C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:19][CH2:20]2)=[O:10])[C@H:4]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([N+:39]([O-:41])=[O:40])[CH:34]=2)[C:3]=1[C:42]([O:44][CH3:45])=[O:43]

Participants

6

Reactant 4

HCID 238314-(2-Hydroxyethyl)-1-piperazineethanesulfonic acidHCID 24766Chondroitin SulfateHCID 6918096Dexniguldipine hydrochlorideHCID 73357449Tetrasodium;1-methylnonane-1,3,5,7-tetracarboxylate2×

Product 1

HCID 6918097(+)-Niguldipine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Various other hydrophilic polymers were investigated for there use in producing dispersions of Dexniguldipine Hydrochloride. 0.1 mL of a solution containing 2 mg/mL Dexniguldipine Hydrochloride in 50% aqueous DMSO was added to 1 mL of HEPES-NS containing 10 mg of one of the following polymers: Chondroitin Sulfate A, Dextran Sulfate, polyacrylic acid sodium salt (MW 150,000), polyacrylic acid sodium salt (MW 2000) or Dextran (MW 70,000). A control group containing no polymer was also investigated. Each mixture was vortexed for 1 minute and allowed to sit for 24 hours at room temperature. After this time period the mixtures were votexed again for 15 minutes after which the quality and stability of the dispersions were visually evaluated. Stable dispersions were produced only in the mixtures that contained polyanions.

Workup

  1. additionA control group containing no polymer
  2. waitto sit for 24 hours at room temperature
  3. waitAfter this time period the mixtures were votexed again for 15 minutes
  4. customStable dispersions were produced only in the mixtures that

Sources & evidence

ORD record
ord-16999cd43a52480d83668d5f1b56698a
Source dataset
uspto-grants-2000_04
Patent number
US06048550

Reaction notes

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