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Sapropterin
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Synonyms:
Tetrahydrobiopterin; THB; BH4; Dapropterin; (6R)-L-erythro-tetrahydrobiopterin
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ATC:
A16AX07
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Use:
Lorem
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Chemical name:
Lorem ipsum dolor sit amet, consetetur sadipscing elitr, sed diam
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Formula:
Lorem ipsum dolor sit amet,
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MW:241.25 g/mol
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CAS-RN:62989-33-7
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InChI Key:FNKQXYHWGSIFBK-RPDRRWSUSA-N
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InChI:InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1
Derivatives
Dihydrochloride
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Formula:
C9H15N5O3 • 2HCl
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MW:314.17 g/mol
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CAS-RN:69056-38-8
Synthesis Path
- Process with D-ribose as starting material according to WO 2016 189542 (Natco Pharma Ltd.) and US 5 043 446 (Nisshin Flour Milling) can be considered as the most economical one. Practically all described syntheses of THB aim at L-erythro-biopterin as precursor substance.
Substances Referenced in Synthesis Path
| CAS-RN |
Formula |
Chemical Name |
CAS Index Name |
| 50-69-1 |
C5H10O5 |
D-ribose |
|
| 13199-25-2 |
C8H14O5 |
2,3-O-isopropylidene-D-ribose |
|
|
C9H18O5 |
1-deoxy-3,4-O-isopropylidene-D-allitol |
|
|
C8H14O4 |
5-deoxy-2,3-O-isopropylidene-D-ribose |
|
| Lorem |
Lorem |
Lorem |
Lorem |
| Lorem |
Lorem |
Lorem |
Lorem |
| Lorem |
Lorem |
Lorem |
Lorem |
| Lorem |
Lorem |
Lorem |
Lorem |
| Lorem |
Lorem |
Lorem |
Lorem |
| Lorem |
Lorem |
Lorem |
Lorem |
Trade Names
| Country |
Trade Name |
Vendor |
Annotation |
| USA |
Lorem |
Lorem
|
|
| EU |
Lorem |
Lorem
|
|
(wfm = withdrawn from market)
Formulations
- Loremipsumdolorsitamet,consetetursadipscingelitr,sed
References
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- US 9 999 999 (Nisshin Flour Milling; 27.08.1991; JP-prior. 28.02.1989).
- WO 9999 999999 A1 (Natco Pharma Ltd.; publ. 01.12.2016; IN-prior. 28.05.2015; internat. filing date 22.07.2015).
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Syntheses starting from 5-deoxy-L-arabinose:
- Patterson, E.L. et al., J. Am. Chem. Soc., (1956) 78, 5868.
- US 9 999 999 (Smith Kline & French; 1970; USA-prior. 1968).
- Taylor, E.C. and Jacobi, P.A., J. Am. Chem. Soc., (1974) 96, 6781.
- Matsuura, S. et al., Bull. Chem. Soc. Jpn., (1975) 48, 3767.
- Viscontini, M. et al., Helv. Chim. Acta, (1977) 60, 211.
- Fernandez, A.-M. and Duhamel, L., J. Org. Chem., (1996) 61, 9999 - synthesis starting from L-tartaric acid via 5-deoxy-L-arabinose.
- US 9 999 999 (Shiratori Pharm.; 22.04.2008; JP-prior. 27.12.2004).
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Synthesis starting from L-arabinose:
- EP 999 999 (Kanegafuchi; 06.02.1991; JP-prior. 21.06.1984).
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Hydrogenation of L-erythro-biopterin:
- EP 999 999 (Shiratori Pharm.; 14.08.1991; JP-prior. 28.01.1985).
- US 9 999 999 (Kanegafuchi; 17.06.1986; JP-prior. 23.02.1984).
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Formulation:
- US 9 999 999 (BioMarin; 28.07.2009; USA-prior. 17.11.2004) - stable tablets.
- US 9 999 999 (BioMarin; 22.12.2015; USA-prior. 02.11.2011) - dry blend powder.
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Medical use:
- US 9 999 999 (BioMarin; 28.07.2009; USA-prior. 17.11.2003).
- US 9 999 999 (BioMarin; 03.11.2009; USA-prior. 11.04.2007).
