PATENT CLAIM ANALYSIS

Application Number: 15891433
Application Type: Utility
Filing Date: 2018-02
Publication Date: 2018-09
Patent Classification: ["548", "300100"]

Abstract:
The invention relates to a compound of the 5-acylsulfanyl-histidine type and the derivatives thereof, of general formula (I), wherein R1 to R3=H, alkyl, especially CH3; R4=H, alkyl, especially CH3, alkyle(C=0), substituted alkyl (C═O), aryl (C═O); β-alanyl (H2NCH2CH2 (C═O); α-amino-acyl; R5=alkyl, especially methyl, phenyl. The invention also relates to the use of said compound for producing compounds of the 5-sulfanyl-histidine type and the derivatives thereof, in addition to corresponding disulfides; and to the various methods for the production thereof.

Claim (Index 29):
\u201cOne-pot\u201d method (D) for preparing the 5-sulfanyl-histidine compounds of formula (II) as defined in  claim 21 , and their corresponding disulfides from the corresponding histidine compounds, by combining the following methods:\n (A) a method_(A) for preparing the 5-acylsulfanyl-histidine compounds of formula (I), \n Where R1 to R4 are as defined for the compounds of formula (II) and R5 is alkyl or phenyl;\n as well as all the stereoisomers, diastereoisomers and enantiomers, in particular in terms of the carbon atom bearing the COOH group, taken separately or in a mixture; and all the salts of pharmaceutically acceptable acids of said compound of general formula (I), characterized in that said method is comprising the following steps: \n 1) The reaction of the histidine, racemic (DL) or one of the enantiomers thereof (D or L), or \n one of their compounds alkylated on the nitrogen in position 1 of the imidazole ring, racemic (DL) or one of the enantiomers thereof (D or L), or \n one of their compounds alkylated or acylated on the nitrogen of the \u03b1-amine function, racemic (DL) or one of the enantiomers thereof (D or L), or \n one of their compounds alkylated on the nitrogen in position 1 of the imidazole ring and alkylated or acylated on the nitrogen of the \u03b1-amine function, racemic (DL) or one of the enantiomers thereof (D or L), \n in the presence of 1 to 2 equivalents of mineral or organic acid, with \n a) an agent generating halogenium ions X+ in a polar protic solvent, at temperatures of 0-25\u00b0 C., then with \n b) a sulfur-containing reagent of the carbothioic acid type of formula alkyl or phenyl C(\u2550O)SH or one of the salts thereof in a polar protic solvent, \n then, \n 2) optionally, the purification by column liquid chromatography or any other purification method well known to the person skilled in the art. with \n (B) a method (B) for preparing the 5-sulfanylhistidine compounds of formula (II) obtained from the 5-acylsulfanyl-histidine compounds of formula (I) described in method (A), characterized in that said method comprising the following steps:\n 1) Either directly (method B1): \n e) by hydrolysis of the 5-acylsulfanyl-histidine compound obtained in a polar protic solvent by stirring at a temperature above 20\u00b0 C. in the presence of a thiol, \n f) then, optionally, purification by column liquid chromatography or any other purification method well known to the person skilled in the art. \n 2) Or indirectly (method B2): \n f) by hydrolysis of the 5-acylsulfanyl-histidine compound obtained in a polar protic solvent by stirring at a temperature above 20\u00b0 C. in order to obtain the corresponding disulfide, \n g) then reduction of the disulfide by reaction with a thiol, \n h) then, optionally, purification by column liquid chromatography or any other purification method well known to the person skilled in the art; \n or with (C) a method (C) characterized in that said method comprises the following steps:\n in the presence of 1 to 2 equivalents of mineral or organic acid, the reaction with: \n c) an agent generating halogenium ions X + in a polar protic solvent, at a temperature of 0-25\u00b0 C., then with \n d) a sulfur-containing reagent of the carbothioic acid of formula alkyl or phenyl C(\u2550O)SH or one of the salts thereof in a polar protic solvent, \n followed by \n 1) Either: \n g) the hydrolysis of the 5-acylsulfanyl-histidine compound obtained in a polar protic solvent by stirring at a temperature between 70 and 130\u00b0 C. in the presence of a thiol,\n h) then, optionally, the purification by column liquid chromatography or any other purification method well known to the person skilled in the art. \n 2) Or: \n j) by hydrolysis of the 5-acylsulfanyl-histidine compound obtained in a polar protic solvent by stirring at a temperature between 70 and 130\u00b0 C. in order to obtain the corresponding disulfide, \n k) then, optionally, purification by column liquid chromatography or any other purification method well known to the person skilled in the art.

Metadata:
- Claim Count in Document: 8.0
- Percentile: 88.0
- Lexical Diversity: 2.0566
- Patent Class: 548.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: True
- Related Applications: ['15314628', '15302633', '15513237', '13320519', '15778168']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.6633677793583479
- 35 USC 102 Novelty (BERT): 0.6121197280035782
- Combined Prediction Score: 0.6582429742228709
- Mean Citation Score: 278.401542
- Max Citation Score: 572.84045
- Similarity Product: 470.8515448775918

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 0

Dataset: test