PATENT CLAIM ANALYSIS

Application Number: 15767966
Application Type: Utility
Filing Date: 2018-04
Publication Date: 2018-10
Patent Classification: ["564", "501000"]

Abstract:
The present invention relates to an industrial process for the preparation of (5S,10S)-10-benzyl-16-methyl-11,14,18-trioxo-15,17,19-trioxa-2,7,8-trithia-12-azahenicosan-5-aminium (E)-3-carboxyacrylate salt of following formula (I): wherein X is fumarate. This process comprises the following successive key steps: a kinetic resolution, formation of disulfide compound, peptide coupling, and anion exchange reaction to obtain the desired product of formula (I).

Claim (Index 1):
Industrial process for the preparation of (5S,10S)-10-benzyl-16-methyl-11,14,18-trioxo-15,17,19-trioxa-2,7,8-trithia-12-azahenicosan-5-aminium (E)-3-carboxyacrylate salt of following formula (I): comprising the following successive synthetic steps performed in degassed organic polar or apolar, protic or aprotic solvents: 1. Preparing compound E of following formula with an enantiomeric excess higher than 95% by 1a) Reacting A of following formula With 0.5-0.6 molar equivalents of quinine in organic polar and aprotic solvents; 1b) Crystallizing the resulting quinine salt at temperature ranging from 10\u00b0 C. to 20\u00b0 C., in same organic solvent than the one used in step 1a, wherein crystallization is initiated by adding few crystals of the desired enantiomer salt to initiate the crystallization, then; 1c) Recrystallizing the salt obtained after step 1b at the same temperature range and same solvent than the one used in step 1 b; 1d) Recovering of compound E by:\n 1d.1) recovering compound (D) of following formula \n 1d.2) deprotecting thiolacetate in polar and protic solvent such as MeOH; 1e) Recovering of quinine; 2. Preparing compound F of following formula By 2a) Reacting first 1.1 molar equivalents of said compound E with 1 molar equivalent of chlorocarbonyl sulfenyl chloride, in polar and aprotic solvent, then; 2b) Reacting the intermediate obtained after step 2a with 0.9 molar equivalents of compound B of following formula In solution with 1 molar equivalent of Et 3 N in same solvent than the one used in step 2a; 3. Preparing compound G of following formula By Reacting said compound F with amino-ester C of following formula, wherein Y \u2212  is an anion: In polar solvent; 4. Then, recovering salt (I) of followed formula By 4a) adding 5 molar equivalent of formic acid on said compound G; 4b) exchanging the formiate by a fumarate using a continuous flow technology.

Metadata:
- Claim Count in Document: 47.0
- Percentile: 91.0
- Lexical Diversity: 1.40816
- Patent Class: 564.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: True
- Related Applications: ['13144391', '14001756', '13879258', '14367216', '15935558']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.686825294852049
- 35 USC 102 Novelty (BERT): 0.5127634983350736
- Combined Prediction Score: 0.6694191152003515
- Mean Citation Score: 184.35517
- Max Citation Score: 192.49998
- Similarity Product: 126.01474838526606

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

Dataset: test