http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-3983118-A

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filingDate 1974-08-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1976-09-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_9f253b444cad15bef93c45e446bf6812
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publicationDate 1976-09-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-3983118-A
titleOfInvention Production of N5 -methyltetrahydrohomofolic acid and related reduced derivatives of homofolic acid
abstract The preparation of N5-methyltetrahydrohomofolic acid and alkali metal salts thereof is from homofolic acid starting material (HFA) by catalytic reduction with platinum oxide in the dark under hydrogen at a slight overpressure to produce tetrahydrohomofolate (THHF), them immediately reacting this product with formaldehyde to produce 5,11-methylenetetrahydrohomofolate and reducing this methylene intermediate without isolation with sodium borohydride to give the desired 5-methyltetrahydrohomofolate in the disodium salt form. The 5-methyl product is recovered by precipitating side products at a pH of about 3.8 with acetic acid and refrigerating the product filtrate overnight at about 3 DEG -10 DEG C. The filtrate containing the product 5-methyltetrahydrohomofolate (5-MeTHHF) is treated with charcoal, concentrated to an oil and the 5-methyl product is precipitated with absolute ethanol. The 5,11-methylenetetrahydrofolate may be separately recovered and in a second reaction an additional product known as the 5,11-methenyl is formed by reaction with formic acid. These products show increased stability over folate analogues and show biological promise in the treatment of cancer and leukemia as antifolates and specifically against L1210-FR8 tumor in mice.
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priorityDate 1972-06-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ03LN3
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6LUM1
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ74IU3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB7MZC6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ1Q8B2
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5E7P1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5PEN6
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID33499
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5X119
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA6M378
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA2SHH0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC4L1C9
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http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID425193155
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA4WE03
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http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID128025068
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ1LSU0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC3PEY5
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6G2S8
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID22171
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID31923417
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID3920216
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ0HG85
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP90463
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB7V2Q5
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA7NB78
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA1KAF7
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ49XN8
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP48464
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ03YZ8
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID2897608
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ667F9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA4WQT6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP0A885
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC6DAE9
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID60500458
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5L9L6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ32C94
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID740018
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP0A886
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB8D7X0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ92AD4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA5VCW6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC0QWM9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA5VJK9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ21NW5
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ2NRH3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC1KWH4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ4JX59
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID56942525
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ8EH94
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA4SVT7
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA1KMA6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ9PB13
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB0CHI7
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID226442588
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC5DAR2
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ134B1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ2K6G8
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID414803645
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ73VZ2
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB7NVX2
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCNP_067263
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA5VRE7
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID918188
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ7VMH2
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ2W7P4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6KIQ6
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID415751178
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC0RE38
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID419559485
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC4LD19
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB0TYI1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ8P1D1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ9Z671
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ58167
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ834R3
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA1KVB3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCO96650
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID419581977
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http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID1451373
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http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP57515
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ2FH11
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ9N1D3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ3JEI2
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ9K7B5
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ0ABR1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ9A6H0
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID45426752
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID33062960
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA1R8Y7
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ3SH96
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ21U56
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ1ME82
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6NIF2
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP09249
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA4TCI9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5WDS1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ8PP46
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA5WAK1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP44420
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5F732
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ89940
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID507631
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ0AHA4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ12CI6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ47Y31
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB7VJ78
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6A761
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ57CA9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA4TLC5
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB7UHP4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5D189
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA0Q7B4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5P233
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP47469
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ5ZRL3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ2NZH9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA6VMA0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA7MR31
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA5WHY0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ65J44
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA8GIH7
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID57973851
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB3QZX0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ03F96
http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID783
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC1CQE7
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ87UL4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB9JH03
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID226433976
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA1AWQ8
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ1GFV4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA6W1R4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA6GWH3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ87SA0
http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID135436548
http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID702
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ31XG0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ738X7
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID7298
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCC0PXI9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ8EQG0
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCP57808
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ7VUE3
http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID22892188
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ9JT57
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA0QIU1
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6REU8
http://rdf.ncbi.nlm.nih.gov/pubchem/compound/CID135436541
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA0QVR9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ64PV5
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA8AP42
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ12KG8
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ6HJC7
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB8GN06
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID879417
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA6WKP4
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA9L5M3
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB7LY83
http://rdf.ncbi.nlm.nih.gov/pubchem/substance/SID425901710
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA4VGL9
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCA6WGF9
http://rdf.ncbi.nlm.nih.gov/pubchem/gene/GID11771535
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ8NS38
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCB1IU17
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ8Y0U6
http://rdf.ncbi.nlm.nih.gov/pubchem/protein/ACCQ97EV3

Total number of triples: 594.