146464-92-8

Basic information

• Product Name: 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-yl-
• Synonyms: 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-yl-;6-Pteridinepropanoic acid, 2,4-diaMino-a-(4-carboxyphenyl)-a-2-propynyl-;6-Pteridinepropanoic acid, 2,4-diaMino-α-(4-carboxyphenyl)-α-2-propyn-1-yl-;4-(2-Carboxy-1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid;10-Propargyl-10-carboxy-4-deoxy-4-amino-10-deazapteroic acid;2,4-Diamino-alpha-(4-carboxyphenyl)-alpha-2-propynyl-6-pteridinepropanoic acid
• CAS NO: 146464-92-8
• Molecular Formula: C₁₉H₁₆N₆O₄
• Molecular Weight: 392.36814
• Mol File: 146464-92-8.mol

Chemical Properties

• Boiling Point: 718.9±70.0 °C(Predicted)
• Appearance: /
• Density: 1.555±0.06 g/cm3(Predicted)
• PKA: 2.65±0.10(Predicted)
• CAS DataBase Reference: 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-yl-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-yl-(146464-92-8)
• EPA Substance Registry System: 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-yl-(146464-92-8)

Safety Data

• Hazardous Substances Data: 146464-92-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-ylis used as a potential pharmaceutical agent for its possible biological activity. 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-yl-'s unique structure may offer novel therapeutic properties, which could be harnessed for the development of new drugs or treatments.
Used in Biochemical Research:
In the field of biochemistry, 6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-ylis utilized as a subject of study to understand its interactions with biological systems. Its structural complexity may provide insights into new mechanisms of action or reveal its role in biochemical processes.
Used in Chemical Synthesis:
6-Pteridinepropanoic acid, 2,4-diamino-.alpha.-(4-carboxyphenyl)-.alpha.-2-propyn-1-ylcan be employed as a building block or intermediate in the synthesis of more complex organic compounds. Its unique functional groups may facilitate the creation of new chemical entities with specific applications in various industries.

Upstream product

• 501-89-3 4-(carboxymethyl)benzoic acid 
• 1548618-47-8 10-propargyl-10-carbomethoxy-4-deoxy-4-amino-10-deazapteroic acid methyl ester hydrobromide salt 
• 146464-90-6 α-propargylhomoterephthalic acid dimethyl ester 
• 52853-40-4 6-bromomethyl-2,4-diaminopteridine hydrobromide 
• 52787-14-1 methyl 4-(2-methoxy-2-oxoethyl)benzoate 
• 146464-91-7 methyl-4-(2-((2,4-diaminopteridin-6-yl)methyl)-1-methoxy-1-oxopent-4-yn-2-yl)benzoate 

Downstream Products

• 374777-77-2 10-propargyl-10-deazaaminopterin dimethyl ester 
• 1320211-82-2 C₂₅H₂₇N₇O₅ 
• 1320211-79-7 C₂₅H₂₇N₇O₅ 
• 1445586-53-7 lithium 10-propargyl-4-deoxy-4-amino-10-deazapteroate 
• 1445586-50-4 10-propargyl-10-carboxy-4-deoxy-4-amino-10-deazapteroic acid sodium salt 
• 1445586-43-5 4-(3-((2,4-diaminopteridin-6-yl)methyl)-5-methylene-2-oxotetrahydrofuran-3-yl)benzoic acid 
• 146464-93-9 4-(1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl)benzoic acid 
• 1445586-44-6 potassium 10-propargyl-4-deoxy-4-amino-10-deazapteroate 
• 146464-91-7 methyl-4-(2-((2,4-diaminopteridin-6-yl)methyl)-1-methoxy-1-oxopent-4-yn-2-yl)benzoate 
• 146464-94-0 10-propargyl-10-deazaaminopterin diethyl ester 
• 146464-95-1 pralatrexate 
• 948552-65-6 C₂₃H₂₄N₆O₄ 

Relevant articles and documents

A suitable industrial production pula Qu Sha method for the preparation of

The invention relates to the field of pharmaceutical chemistry technology, and more specifically relates to an anticarcinogen 10-Propargyl-10-deazaaminopterin (Pralatrexate) and synthesis of an intermediate thereof. The invention has the advantages of simple operation, low contents of related impurities, easiness in purification of intermediate, thereby avoiding purification mode of column chromatography, and the invention can be applied to large scale production of Pralatrexate bulk drug as well as preparation and purification method of important intermediates.

IMPROVED PROCESS FOR THE PREPARATION OF PRALATREXATE

An improved process for the preparation of Pralatrexate which is less hazardous. The invention further relates to novel intermediates and process thereof useful for the preparation of Pralatrexate. The present invention also relates to a substantially pure Pralatrexate and a process for obtaining the same in high yield.

IMPROVED PROCESS FOR THE PREPARATION OF PRALATREXATE

An improved process for the preparation of Pralatrexate which is less hazardous. The invention further relates to novel intermediates and process thereof useful for the preparation of Pralatrexate. The present invention also relates to a substantially pure Pralatrexate and a process for obtaining the same in high yield.

PROCESS FOR PRALATREXATE

The present invention provides a novel process for the purification of alpha-propargylhomoterephthalic acid dimethyl ester substantially free of homoterephthalic acid dimethyl ester. The present invention also provides a novel process for the purification of pralatrexate.

PROCESSES AND INTERMEDIATES FOR PREPARING PRALATREXATE

Processes for preparing and purifying Pralatrexate are described in the present application, as well as intermediates in these processes, and salts and solid state forms of the Pralatrexate intermediates.

Optically Pure Diastereomers of 10-Propargyl-10-Deazaaminopterin and Methods of Using Same

The present invention relates to diastereomers of 10-propargyl-10-deazaminopterin, compositions comprising optically pure diastereomers of 10-propargyl-10-deazaminopterin, in particular the two (R,S) diastereomers about the C10 position. Methods of preparation of these diastereomers, compositions containing them, and their use for the treatment of conditions related to inflammatory disorders and cancer are also disclosed.

Treatment of T-cell lymphoma using 10-propargyl-10-deazaaminopterin

T cell lymphoma is treated by administering to a patient suffering from T cell lymphoma a therapeutically effective amount of 10-propargyl-10-deazaaminopterin. Remission is observed in human patients, even with drug resistant T cell lymphoma at weekly dosages levels as low as 30 mg/m2. In general, the 10-propargyl-10-deazaaminopterin is administered in an amount of from 30 to 275 mg/m2 per dose.

Synthesis and in vitro antitumor activity of new deaza analogues of the nonpolyglutamatable antifolate Nα-(4-amino-4-deoxypteroyl)-Nδ- hemiphthaloyl-L-ornithine (PT523)

Details are disclosed for the synthesis of Nα-[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]-N δ-hemiphthaloyl-L-ornithine (2) and Nα-[4-[5-(2,4-diaminoteridin-6-yl)pent-1-yn-4-yl]benzoyl]-N δ-hemiphthaloyl-L-

Synthesis and antitumor activity of 10-propargyl-10-deazaaminopterin

Successive alkylation of dimethyl homoterephthalate with propargyl bromide and 2,4-diamino-6-(bromomethyl)pteridine followed by ester saponification at room temperature afforded 2,4-diamino-4-deoxy-10-carboxy-10-propargyl-10- deazapteroic acid. The 10-COOH was readily decarboxylated by heating in DMSO at a temperature of only 120 °C to yield the diamino-10-propargyl-10- deazapteroic acid intermediate. Coupling with diethyl L-glutamate and ester hydrolysis gave the title compound. The 10-propargyl analogue was about 5 times more potent than MTX as an inhibitor of growth in L1210 cells, but was only one-third as potent as an inhibitor of DHFR from L1210. The analogue was transported inward very effectively in L1210 cells showing a 10-fold advantage over MTX. At a dose of 36 mg/kg the 10-propargyl compound caused shrinkage of the E0771 solid murine mammary tumor to only 1% of untreated controls.