945-24-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE is used as an impurity in Methotrexate, which is a medication used to treat various conditions such as cancer, autoimmune diseases, and psoriasis. Its presence as an impurity may affect the efficacy and safety of the drug, making it important to monitor and control its levels during the manufacturing process.
Used in Antiparasitic Drug Development:
2,4-DIAMINO-6-(HYDROXYMETHYL)PTERIDINE is used as a reagent for the development of selective antiparasitic compounds. Its unique chemical structure and properties make it a promising candidate for the design and synthesis of new drugs targeting parasitic infections.

InChI:InChI=1/C7H8N6O/c8-5-4-6(13-7(9)12-5)10-1-3(2-14)11-4/h1,14H,2H2,(H4,8,9,10,12,13)

Upstream product

• 73978-41-3 2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride 
• 191786-04-6 N-(2-Butyrylamino-6-hydroxymethyl-pteridin-4-yl)-butyramide 
• 1004-74-6 2,4,5,6-tetraaminopyrimidine 
• 96-26-4 dihydroxyacetone 
• 59-05-2 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid 
• 522614-11-5 N-{[(acetyloxy)methyl]-4-[2-(4-nitrophenyl)ethoxy]pteridin-2-yl}acetamide 
• 52-89-1 l-cysteine hydrochloride 
• 5392-28-9 2,4,5,6-tetraaminopyrimidine sulfate 
• 712-29-8 6-(hydroxymethyl)pterin 
• 32363-58-9 N-{6-[(acetyloxy)methyl]-3,4-dihydro-4-oxopteridin-2-yl}acetamide 
• 52853-40-4 6-bromomethyl-2,4-diaminopteridine hydrobromide 
• 191786-01-3 β-(2,4-diamino-6-pteridinyl)-p-ethylstyrene 
• 39944-62-2 2,4,5,6-tetraamino-pyrimidine dihydrochloride 
• 10318-18-0 DL-cysteine hydrochloride 

Downstream Products

• 57521-63-8 2,4-diamino-6-chloromethylpteridine 
• 19741-14-1 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid 
• 79640-70-3 (S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid 
• 23853-09-0 4-[(2,4-diaminopteridin-6-ylmethyl)-N-methylamino]benzoic acid methyl ester 
• 54-62-6 aminopterin 
• 95484-99-4 α-methyl γ-tert-butyl N-(4-amino-4-deoxy-N¹⁰-formylpteroyl)-L-glutamate 
• 95485-00-0 γ-tert-butyl N-(4-amino-4-deoxy-N¹⁰-formylpteroyl)-L-glutamate 
• 95484-98-3 γ-tert-butyl N-(4-amino-4-deoxypteroyl)-L-glutamate 
• 95485-01-1 p-nitrophenyl 4-amino-4-deoxy-N¹⁰-formylpteroate 
• 79640-68-9 α-methyl γ-tert-butyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-glutamate 
• 79640-76-9 γ-tert-butyl N-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-glutamate 
• 89043-75-4 4-amino-4-deoxy-N¹⁰-formylpteroic acid 
• 36093-85-3 4-amino>benzoic acid 
• 43111-51-9 ethyl 4-amino-4-deoxy-N¹⁰-methylpteroate 

Relevant academic research and scientific papers

ANTIFOLATE-CARRYING NANOPARTICLES AND THEIR USE IN MEDICINE

The present invention provides a nanoparticle comprising: a core comprising a metal and/or a semiconductor; and a plurality of ligands covalently linked to the core, wherein said ligands comprise: (i) at least one dilution ligand comprising a carbohydrate, glutathione or an ethylene glycol-containing moiety; and (ii) a ligand of the formula D-L1-Z-L2, wherein D comprises an antifolate drug or folic acid, L1 comprises a first linker portion comprising a C2-C12 glycol and/or C2-C12 alkyl chain, L2 comprises a second linker portion comprising a C2-C12 glycol and/or C2-C12 alkyl chain, wherein L1 and L2 may be the same or different, and wherein Z represents a carbonyl-containing group linking L1 and L2, and wherein L2 is coupled to said core, Also provided are pharmaceutical compositions comprising such nanoparticles, medical uses thereof and methods for producing the nanoparticles.

Synthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis

A series of novel hydrogen peroxide sensitive prodrugs of methotrexate (MTX) and aminopterin (AMT) were synthesized and evaluated for therapeutic efficacy in mice with collagen induced arthritis (CIA) as a model of chronic rheumatoid arthritis (RA). The prodrug strategy selected is based on ROS-labile 4-methylphenylboronic acid promoieties linked to the drugs via a carbamate linkage or a direct C-N bond. Activation under pathophysiological concentrations of H2O2 proved to be effective, and prodrug candidates were selected in agreement with relevant in vitro physicochemical and pharmacokinetic assays. Selected candidates showed moderate to good solubility, high chemical and enzymatic stability, and therapeutic efficacy comparable to the parent drugs in the CIA model. Importantly, the prodrugs displayed the expected safer toxicity profile and increased therapeutic window compared to MTX and AMT while maintaining a comparable therapeutic efficacy, which is highly encouraging for future use in RA patients.

PRODRUGS ACTIVATED BY REACTIVE OXYGEN SPECIES FOR USE IN THE TREATMENT OF INFLAMMATORY DISEASES AND CANCER

Prodrugs activated predominantly or exclusively in inflammatory tissue, more particularly prodrugs of methotrexate and derivatives thereof, which are selectively activated by Reactive Oxygen Species (ROS) in inflammatory tissues associated with cancer and inflammatory diseases, as well as method for preparing said prodrugs.

Tetrahydrofurfuroxy folic acid analogue synthetic method

The invention relates to a novel method for synthesis of tetrahydrofolic acid analogues, and mainly solves the problems of uneasily controllable reaction conditions and many produced by products in a conventional synthesis method. A series of tetrahydrofolic acid analogues are prepared by employing 5-aminouracil or 2,4,5,6-tetraaminopyrimidine, 2,5,6-triamino-4-hydroxypyrimidine as an initial raw material and combining the steps of cyclization, oxidation, chlorination, ammonolysis, catalytic hydrogenation reduction, intramolecular cyclization, aziridine ring opening, nucleophilic substitution, ethoxycarbonyl hydrolysis, etc. Compared with a conventional synthesis method, the novel method provided by the invention has the characteristics of mild and stable reaction conditions, few by-products, wide application range, etc.

DIAMINOPTERIDINE DERIVATIVES

The present invention relates novel diaminopteridine derivatives, their compositions and method of treatment comprising the same for use as anti-infectives.

USE OF THE STAUDINGER LIGATION IN IN VIVO ASSEMBLY OF A BIOLOGICALLY ACTIVE COMPOUND

The invention provides methods and tools for the in vivo self-assembly of drugs. This makes it possible to reduce problems associated with the lack of selectivity, reduced solubility and other disadvantages of intact drugs.

Aminopterin dosage forms and methods for inflammatory disorders

Embodiments of the present invention provide dosage forms and methods for treating a patient with an inflammatory disorder with a therapeutically effective amount of aminopterin, or a pharmaceutically acceptable salt thereof, that achieve efficacy without concomitant toxicity. Within certain embodiments, the present invention provides a method for treating an inflammatory disorder in a patient with uninterrupted doses of aminopterin.

Compositions and methods employing aminopterin

The present invention relates to pharmaceutical compositions containing the antifolate aminopterin, processes for making the compositions, and methods of using them to treat disorders in adult and pediatric patients. Pharmaceutical compositions substantially free of impurities are provided comprising a therapeutically effective amount of aminopterin, or a pharmaceutically acceptable salt thereof. Relative to the teachings of the prior art, the disclosed methods and compositions provide unexpected improvements that include a greater interpatient oral bioavailability in pediatric patients, a smaller interpatient coefficient of variation of oral bioavailability, a smaller mean intrapatient coefficient of variation of oral bioavailability, a greater therapeutic index, a smaller coefficient of variation of toxicity, efficacy in combination therapy, and efficacy of certain polyglutamated metabolites.

Methods of treating inflammatory diseases with ammonium salts of ornitihine derivatives

The present invention relates to pharmaceutically active ornithine compounds, particularly to pharmaceutically acceptable ammonium salts of Nδ-acyl derivatives of Nα(4-amino-4-deoxypteroyl)-L-ornithine compounds; and methods of treatment and pharmaceutical compositions that utilize or comprise one or more of such ammonium salts. The ammonium salts provided by the invention exhibit superior chemical stability than corresponding acidic Nδ-acyl derivatives of Nδ-acyl derivatives of Nα(4-amino-4-deoxypteroyl)-L-ornithine compounds.

Pteridines. Part CXIII. Protection of Pteridines

The low solubulity of pterins can drastically be improved by N2-acylation or formation of the N2-[(dimethylamino)methylene] derivatives. Both types of compounds can be alkylated under Mitsunobu conditions to form from N2-acylpterins (see 2 and 3) and their derivatives (see 5, 6, 8, 9, 11, 13, 15, and 17) selectively the O4-alkyl derivatives 22-31, whereas the electron-donating [(dimethylamino)methyleneamino] function in 46-51 gives, in a selective reaction, the N(3)-substitution (->52-61). N2,N2-Dimethylpterins and 18 and 19 and N2-methylpterins 20 and 21 direct alkylation also to the O4-position (->32-35, 38 and 39). Deacylation can be achieved under very mild conditions by solvolysis with MeOH (22->40, 26->41), and displacement of the O4-[2-(4-nitrophenyl)ethyl] group proceeds with ammonia at room temperature to the corresponding pteridin-2,4-diamine 42-45. Cleavage of the N2-[(dimethylamino)methylene] group works well with ammonia (->62-67). The advantage of applying the 2-(4-nitrophenyl)ethyl (npe) group as blocking group is seen in its selective removal by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under aprotic conditions without harming the other substituents.