PATENT CLAIM ANALYSIS

Application Number: 15746338
Application Type: Utility
Filing Date: 2018-01
Publication Date: 2018-07
Patent Classification: ["544", "037000"]

Abstract:
The present invention pertains generally to the field of chemical synthesis, and more particularly to methods of chemical synthesis which include the step of preparing a substituted 10H-phenothiazine-3,7-diamine compound of Formula (1) by a step of selective alkylation by reductive amination, in which the corresponding unsubstituted diamine of Formula (4) is reacted with aldehyde/ketone, under reductive amination conditions. The present invention also relates to such methods which incorporate additional subsequent and/or preceding steps, for example, to prepare compounds of Formulae (2) and (3) from compounds of Formula (1), and to prepare compounds of Formula (4) from, for example, compounds of Formulae (5), (6), (7), (8), and (9). Compounds of Formula (1), Formula (2), and Formula (3) are useful, for example, in the treatment of diseases of protein aggregation, such as Alzheimer's disease.

Claim (Index 72):
A method of synthesis of a compound of Formula (1): comprising the step of: reductive amination, in which a compound of Formula (4): is reacted with aldehyde/ketone and a reductive amination agent, under reductive amination conditions, to give the corresponding compound of Formula (1), wherein a carbonyl group, (O\u2550)C<, of the aldehyde/ketone gives rise to a corresponding nitrogen substituent, \u2014CH<; wherein:\n R 1A  is independently a substituent with one point of attachment, wherein the attachment is via a \u2014CH< group; and \n R 1B  is independently H or a substituent with one point of attachment, wherein the attachment is via a \u2014CH< group; \n or \n R 1A  and R 1B , taken together, form a substituent with two points of attachment, wherein each of the attachments is via a \u2014CH< group; \n R 2A  is independently a substituent with one point of attachment, wherein the attachment is via a \u2014CH< group; and \n R 2B  is independently H or a substituent with one point of attachment, wherein the attachment is via a \u2014CH< group; \n or \n R 2A  and R 2B , taken together, form a substituent with two points of attachment, wherein each of the attachments is via a \u2014CH< group; \n and wherein:\n R 3  is independently \u2014H, \u2014R T3 , \u2014R T3H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T3 , \u2014NH 2 \u2014NHR T3 , \u2014NR T3 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or C(\u2550O)OR T3 ; wherein each \u2014R T3  is a C 1-10 alkyl group and R T3H  is a C 1-10 haloalkyl group; and \n R 4  is independently \u2014H, \u2014R T4 , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T4 , \u2014NH 2 , \u2014NHR T4 , \u2014NR T4 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T4 ; wherein each \u2014R T4  is a C 1-10 alkyl group and R T4H  is a C 1-10 haloalkyl group; \n and wherein:\n R 5  is independently \u2014H, \u2014R T5 , \u2014R T5B , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T5 , \u2014NH 2 , \u2014NR T5 , \u2014NR T5 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T5 ; wherein each \u2014R T5  is a C 1-10 alkyl group and R T5H  is a C 1-10 haloalkyl group; and \n R 6  is independently \u2014H, \u2014R T6 , \u2014R T6H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T6 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T6 ; wherein each \u2014R T6  is a C 1-10 alkyl group and R T6H  is a C 1-10 haloalkyl group; \n and wherein:\n R 7  is independently \u2014H, \u2014R T7 , \u2014R T7H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T7 , \u2014NH 2 , \u2014NHR T7 , \u2014NR T7 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T7 ; wherein each \u2014R T7  is a C 1-10 alkyl group and R T7H  is a C 1-10 haloalkyl group; and \n R 8  is independently \u2014H, \u2014R T8 , \u2014R T8H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T8 , \u2014NH 2 , \u2014NHR T8 , \u2014NR T8 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T8 ; wherein each \u2014R T8  is a C 1-10 alkyl group and R T8H  is a C 1-10 haloalkyl group. R 4  is independently \u2014H, \u2014R T4 , \u2014R T4H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T4 , \u2014NH 2 , \u2014NHR T4 , \u2014NR T4 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T4 ; wherein each \u2014R T4  is a C 1-10 alkyl group and R T4H  is a C 1-10 haloalkyl group; and wherein:\n R 5  is independently \u2014H, \u2014R T5 , \u2014R T5H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T5 , \u2014NH 2 , \u2014NR T5 , \u2014NR T5 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T5 ; wherein each \u2014R T5  is a C 1-10 alkyl group and R T5H  is a C 1-10 haloalkyl group; and \n R 6  is independently \u2014H, \u2014R T6 , \u2014R T6H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T6 , \u2014NH 2 , \u2014NHR T6 , \u2014NR T6 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T6 ; wherein each \u2014R T6  is a C 1-10 alkyl group and R T6H  is a C 1-10 haloalkyl group; and wherein:\n R 7  is independently \u2014H, \u2014R T7 , \u2014R T7H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T7 , \u2014NH 2 , \u2014NHR T7 , \u2014NR T7 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T7 ; wherein each \u2014R T7  is a C 1-10 alkyl group and R T7H  is a C 1-10 haloalkyl group; and \n R 8  is independently \u2014H, \u2014R T , \u2014R T8H , \u2014F, \u2014Cl, \u2014Br, \u2014I, \u2014OH, \u2014OR T8 , \u2014NH 2 , \u2014NHR T , \u2014NR T8 2 , pyrrolidino, piperidino, morpholino, \u2014C(\u2550O)OH, or \u2014C(\u2550O)OR T8 ; wherein each \u2014R T8  is a C 1-10 alkyl group and R T8H  is a C 1-10 haloalkyl group.

Metadata:
- Claim Count in Document: 68.0
- Percentile: 86.0
- Lexical Diversity: 2.32051
- Patent Class: 544.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: True
- Related Applications: ['14410952', '13063525', '13984841', '15056610', '13241887']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7034367073225232
- 35 USC 102 Novelty (BERT): 0.510968377072129
- Combined Prediction Score: 0.6841898742974837
- Mean Citation Score: 219.46046
- Max Citation Score: 265.7381
- Similarity Product: 182.3570455619276

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

Dataset: test