Methods for the synthesis of pyridoxamine
First Claim
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1. A method for preparing pyridoxamine, or salt thereof, the method comprising the steps of:
- (a) protecting the hydroxyls of a compound of formula (II), or salt thereof, to form a compound of formula (III), or salt thereof;
wherein R at each occurrence is a hydroxyl protecting group;
(b) converting the compound of formula (III), or salt thereof, to a compound of formula (IV), or salt thereof;
wherein represents a cyclic imide substituent;
(c) converting the compound of formula (IV), or salt thereof, to a compound of formula (V) wherein R1 is H or is R, wherein when R1 is R, step (c) is followed by step (d), wherein step (d) comprises;
(d) converting the compound of formula (V), or salt thereof, to pyridoxamine (I), or a salt thereof;
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Abstract
The invention provides non-oxidative methods for the large scale manufacture of pyridoxamine (I) (4-aminomethyl-3-hydroxy-5-hydroxymethyl-2-methylpyridine):
25 Citations
25 Claims
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1. A method for preparing pyridoxamine, or salt thereof, the method comprising the steps of:
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(a) protecting the hydroxyls of a compound of formula (II), or salt thereof, to form a compound of formula (III), or salt thereof;
wherein R at each occurrence is a hydroxyl protecting group;
(b) converting the compound of formula (III), or salt thereof, to a compound of formula (IV), or salt thereof;
wherein represents a cyclic imide substituent;
(c) converting the compound of formula (IV), or salt thereof, to a compound of formula (V) wherein R1 is H or is R, wherein when R1 is R, step (c) is followed by step (d), wherein step (d) comprises;
(d) converting the compound of formula (V), or salt thereof, to pyridoxamine (I), or a salt thereof;
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 13, 14, 18)
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10. A method for preparing pyridoxamine, the method comprising the steps of:
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(a) acylating the hydroxyls of pyridoxine, to form an triester, or salt thereof, of the formula;
(b) treating the triester formed in step (a) with phthalimide, or salt thereof, to form an phthalimido compound, or salt thereof, of the formula;
(c) treating the phthalilimido compound formed in step (b) with a primary amine to form an amide compound, or salt thereof, of the formula;
(d) treating the amide formed in step (c) with a deprotecting agent to form pyridoxamine, or salt thereof. - View Dependent Claims (11, 12)
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- 15. A composition comprising pyridoxamine, or a pharmaceutically acceptable salt thereof, and a compound of the formula (X), or a pharmaceutically acceptable salt thereof:
- 16. A composition comprising pyridoxamine, or a pharmaceutically acceptable salt thereof, and a compound of the formula (XX), or a pharmaceutically acceptable salt thereof:
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17. A composition comprising:
- pyridoxamine, or a pharmaceutically acceptable salt thereof;
a compound of the formula (X), or a pharmaceutically acceptable salt thereof;
and a compound of the formula (XX), or a pharmaceutically acceptable salt thereof - View Dependent Claims (21)
- pyridoxamine, or a pharmaceutically acceptable salt thereof;
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22. A zwitterion of the structure:
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23. A compound of formula (III), or salt thereof:
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wherein R at each occurrence is a hydroxyl protecting group.
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24. A compound of formula (IV), or salt thereof:
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25. A compound of formula (V), or salt thereof:
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wherein R1 is a hydroxyl protecting group.
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Specification