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molecular formula C14H21N3O2S B127528 Sumatriptan CAS No. 103628-46-2

Sumatriptan

Cat. No. B127528
M. Wt: 295.40 g/mol
InChI Key: KQKPFRSPSRPDEB-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US08785396B2

Procedure details

Powder preparation and characterization: Sumatriptan-Na2FDKP powder was prepared as described in Example 9 above, except that the sumatriptan succinate was purchase from LGM Pharma (Boca Raton, Fla.) and L-leucine was added to study whether the aerodynamic performance of the resulting spray-dried powder formed would be improved. Three feed solutions were prepared at 4.5% total solids concentration for a 5 g scale. The feed solutions were prepared by adding FDKP disodium salt, sumatriptan succinate, and L-leucine (0-20 wt %) to de-ionized water with mixing. The solutions were titrated with dilute aqueous ammonia to pH 6.00. The resulting clear feed solutions were vacuum filtered through a 0.2 μm PES filter membrane and spray dried as described in Example 9, however, the drying gas flow was set at 25 kg/hr, the atomization flow was about 4 kg/hr and the atomization pressure was set at 4 bar. The sumatriptan succinate concentration (dry basis) in each solution was 56% to obtain a 40% sumatriptan target load. The powders were analyzed by HPLC, cascade impaction, Karl Fischer titration, scanning electron microscopy (SEM) and tap and bulk density. The results of these studies are shown in Table 9 and FIG. 22.
Quantity
0 (± 1) mol
Type
reactant
Reaction Step One
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0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
total solids
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
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0 (± 1) mol
Type
reactant
Reaction Step Four
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0 (± 1) mol
Type
reactant
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Type
reactant
Reaction Step Four
Name
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Type
solvent
Reaction Step Four
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Five
Yield
40%

Identifiers

REACTION_CXSMILES
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4].C(C(O)=O)CC(O)=O.N[C@H](C(O)=O)CC(C)C.[Na][Na].N>O>[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][CH:14]=[C:13]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]=2[CH:12]=1)(=[O:5])=[O:4] |f:0.1|

Inputs

Step One
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.C(CC(=O)O)C(=O)O
Step Two
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
N[C@@H](CC(C)C)C(=O)O
Step Three
Name
total solids
Quantity
0 (± 1) mol
Type
reactant
Smiles
Step Four
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[Na][Na]
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C.C(CC(=O)O)C(=O)O
Name
Quantity
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Type
reactant
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N[C@@H](CC(C)C)C(=O)O
Name
Quantity
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Type
solvent
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Step Five
Name
Quantity
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Type
reactant
Smiles
N

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
Powder preparation and characterization
ADDITION
Type
ADDITION
Details
was added
CUSTOM
Type
CUSTOM
Details
spray-dried powder
CUSTOM
Type
CUSTOM
Details
formed would
CUSTOM
Type
CUSTOM
Details
The feed solutions were prepared
ADDITION
Type
ADDITION
Details
with mixing
FILTRATION
Type
FILTRATION
Details
filtered through a 0.2 μm PES
FILTRATION
Type
FILTRATION
Details
filter membrane and spray
CUSTOM
Type
CUSTOM
Details
dried
CONCENTRATION
Type
CONCENTRATION
Details
The sumatriptan succinate concentration (dry basis) in each solution

Outcomes

Product
Name
Type
product
Smiles
Name
Type
product
Smiles
CNS(=O)(=O)CC=1C=CC2=C(C1)C(=CN2)CCN(C)C
Measurements
Type Value Analysis
YIELD: PERCENTYIELD 40%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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