Process for preparing tetrahydrobiopterin and analogs of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

Reexamination Certificate

active

07732599

ABSTRACT:
Process for the preparation of tetrahydrobiopterin from neopterin and/or 6-substituted pterins with an improved yield and a high stereoselectivity. Also disclosed herein are novel individual intermediates prepared in the preparation of tetrahydrobiopterin, such as selectively protected neopterin useful for the preparation of tetrahydrobiopterin.

REFERENCES:
patent: 0165595 (1985-12-01), None
patent: 1221380 (1989-09-01), None
Aizpurua et al., “Reaction of Hindered Trialkylsilyl Esters and Trialkylsilyl Ethers with Triphenylphosphine Dibromide: Preparation of Carboxylic Acid Bromides and Alkyl Bromides under Mild Neutral Conditions”,J. Org. Chem., 51(25):4941-4943 (1986).
Ashton et al., “Amino Acid Derivatives of β-Cyclodextrin”,J. Org. Chem., 61(3):903-908 (1996).
Bell et al., “The Reduction of Organic Halogen Compounds by Sodium Borohydride”,J. Org. Chem., 34:3923-3926 (1969).
Blau et al., “Disorders of Tetrahydrobiopterin and Related Biogenic Amines,”The Metabolic and Molecular Bases of Inherited Disease, 8th Ed., Chapter 78, pp. 1725-1776 (2001).
Bradshaw et al., “Synthesis of the Organic Ligand of the Molybdenum cofactor, in protected form”,J. Chem. Soc., 1:3239-3244 (2001).
Bredereck et al., “Darstellung und Eigenschaften der Amidacetale und Aminalester”,Chem. Ber., 101:41-50 (1968).
Chaudhary et al., “4-Dimethylaminopyridine: An Efficient and Selective Catalyst for the Silylation of Alcohols”,Tet. Let., 2:99-102 (1979).
Corey et al., “Protection of Hydroxyl Groups as tert-Butyldimethylsilyl Derivatives”,J. Am. Chem. Soc., 94(17):6190-6191 (1972).
Green et al., “Protective Groups in Organic Synthesis,”Wiley&Sons, 3rd Ed., pp. 201-245 (1999).
Hanaya et al., “Selective N(3)-and O4-Alkylation of L-Biopterin: A Convenient Synthesis of 3-and O4-Methyl-L-biopterin and the Versatile N2-(N,N-dimethylaminomethylene)-N(3)-p-nitrophenethyl-Protected L-Biopterin”,Pteridines, 6(1):1-7 (1995).
Hanessian et al., “Reactions of Carbohydrates with (Halomethylene)dimethyliminium Halides and Related Reagents. Synthesis of Some Chlorodeoxy Sugars”,J. Org. Chem., 34(7):2163-2170 (1969).
Hart et al.,J. Organic. Chem., vol. 68, No. 1, pp. 187-190 (2003).
Hutchins et al., “Sodium Borohydride in Dimethyl Sulfoxide or Sulfolane. Convenient Systems for Selective Reductions of Primary, Secondary and Certain Tertiary Halides and Tosylates”,Tet. Let., No. 40, pp. 3495-3498 (1969).
International Search Report, International Application No. PCT/US2004/038313, dated Jan. 11, 2007.
Kaiser et al., “80. Synthesis of Biopterin from Neopterin? The Formation of Pyrrolo[1,2-ƒ]pteridins upon Side-Chain Activation of Neopterin”,Helv. Chim. Acta., 70:766-770 (1987).
Kim et al., “Direct Conversion of Silyl Ethers into Alkyl Bromides with Boron Tribromide”,J. Org. Chem., 53:3111-3113 (1988).
Kang et al., “Synthesis of 2-ethylthio-6-(3-hydroxy-1,2-O-Isopropylidenepropyl)pteridin-4(3H)-One”,Heterocycles, 53(7):1551-1557 (2000).
Kikuchi et al., “Synthesis of (-)-Biopterin Using (S)-Ethyl Lactate as a Starting Material”,Agric. Biol. Chem., 53(8):2095-2100 (1989).
Larock, “8. Electrophilic Acylation. 1. Synthesis of Aldehydes”,Comprehensive Organic Transformations, Wiley VCH, 2nd Ed., pp. 681-708 (1999).
Mattes et al., “Reactivity of t-butyldimethylsilyl ethers: a facile conversion into bromides”,Tet. Let., 28(15):1697-1698 (1987).
Patterson et al., “The Synthesis of a Pteridine Required for the Growth ofCrithidia fasciculata.”, J. Am. Chem. Soc., vol. 78:5868-5871 (1956).
Pellicciari et al., “Stereospecific Synthesis of the Enantiomers of Nicotinylalanine, a Neuroprotecting Agent”,Tet, Let., 33:3003-3004 (1992).
Ross et al., “Anodic Oxidations. V. The Kolbe Oxidation of Phenylacetic Acid and 1-Methylcyclohexaneacetic Acid at Platinum and at Carbon”,The Journal of Organic Chemistry, 24:2923-2927 (1969).
Russell et al., “Model Studies Related to the Cofactor of the Oxomolybdoenzymes; Part 6: An Improved Synthesis of 6-Substituted Pterins from 2,4,5-Triamino-6-hydroxy-pyrimidine and D-Glucose”,Synlett, pp. 711-712 (1992).
Russell et al., “Model Studies Related to the Cofactor of the Oxomolybdoenzymes. Part 5. Synthesis of 6-Alkenyl- and 6-Alkynylpterins”,Tet. Let., 33(23):3371-3374 (1992).
Schircks et al., “Eine neue, regiospezifische Synthese von L-Biopterin”,Helv. Chim. Acta., 60:211-214 (1977).
Smith et al., “March's Advanced Organic Chemistry, Reactions Mechanisms and Structure,” Wiley & Sons, Inc., 5th Ed., pp. 524-526 (2001).
Soyka et al., “Synthese und Eigenschaften von 5,6-Dihydro-6-(1,2,3-trihydroxypropyl)pteridinen: Kovalente intromolekulare Addukte”,Helv. Chim. Acta., 73:808-826 (1990).
Sugimoto et al., “The Convenient Syntheses of Biopterin and Its Three Opitical Isomers”,Bull. Chem. Soc. Jpn., 48:3767-3768 (1975).
Taylor et al., “An Unequivocal Total Synthesis of L-erythro-Biopterin”,J. Am. Chem. Soc., 96:6781-6782 (1974).
Viscontini et al., “Synthese des natürlichen D-neopterins und L-Monapterins”,Helv. Chim. Acta., 53:1202-1207 (1970).
Viscontini et al., “Eine neue Synthese von D, L-Biopterin”,Helv. Chim. Acta., 55:574-579 (1972).
Written Opinion of the International Searching Authority, International application No. PCT/US2004/038313, dated Jan. 11, 2007.
Zinner et al., “Die partielle Veresterung von D-Arabinose-mercaptalen mit Sulfonsaurechloriden und eine einfache Synthese der 5-Desoxy-D-arabinose”,Chem. Ber., 92:1618-1623 (1959).
Zinner et al., “Synthese and Derivate der 2.5-Didesoxy-D-ribose”,Chem. Ber., 92:2893-2896 (1959).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for preparing tetrahydrobiopterin and analogs of... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing tetrahydrobiopterin and analogs of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing tetrahydrobiopterin and analogs of... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4247507

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.