PATENT CLAIM ANALYSIS

Application Number: 15953428
Application Type: Utility
Filing Date: 2018-04
Publication Date: 2018-11
Patent Classification: ["540", "469000"]

Abstract:
The invention relates to pyrridinobenzodiazepines (PDDs) comprising three fused 6-7-6-membered rings linked to aromatic groups, and pharmaceutically acceptable salts thereof, which are useful as medicaments, such as anti-proliferative agents. PDDs may be represented by formula (I): and salts and solvates thereof, wherein the dotted lines indicates the optional presence of a double bond between one or more of C1 and C2, C2 and C3, and C3 and C4; R1 and R2 are substituent groups; R3 is selected from H, C1-12 alkyl and CH2Ph; R4 is selected from phenyl and Cs-9heteroaryl groups optionally substituted, with the proviso that the optionally substituted C 5-9  heteroaryl is not indolyl; R19 is selected from H and (CH2)t-NR2oR21; Y1 is N or CH; Y2 is N or CH; and wherein at least one of Y1 and Y2 is CH; p is 0 or 1; X1 is a connecting group; L is a linker group; X2 is a connecting group or is absent; q is selected from 0, 1, 2, 3, 4, 5 and 6; A is selected from: for each A1 group one of Y3 and Y4 is selected from N-R17, S and O; and the other of Y3 and Y4 is CH; and Y5 is selected from CH, N, S and COH; for each A2 group one of Y6 and Y7 is independently selected from N and CH; and the other of Y6 and Y7 is CH; R13, R14, R17, R20 and R21 are independently selected from H and C1-6 alkyl; and either: (i) R5 and R6 together form a double bond; (ii) R5 is H and R6 is OH; or (iii) R is H and R6 is OC1-6 alkyl; with the proviso that when p is  0  and A is A 1 , then: (a) for at least one A1 group one of Y Sand Y4 is selected from S and O; or (b) for at least one A1 group Y5 is S; or (c) R4 is not pyrrolyl, imidazolyl, optionally substituted pyrrolyl or optionally substituted imidazolyl.

Claim (Index 1):
A compound of formula (I): and salts and solvates thereof, wherein; the dotted lines indicates the optional presence of a double bond between one or more of C1 and C2, C2 and C3, and C3 and C4; R 1  is selected from R 7 , \u2550CH 2 , \u2550CH\u2014(CH 2 ) m \u2014CH 3 , \u2550O, (CH 2 ) m \u2014OR 7 , (CH 2 ) m \u2014CO 2 R 7 , (CH 2 ) m \u2014NR 7 R 8 , O\u2014(CH 2 ) n \u2014NR 7 R 8 , NH\u2014C(O)\u2014R 7 , O\u2014(CH 2 ) n \u2014NH\u2014C(O)\u2014R 7 , O\u2014(CH 2 ) n \u2014C(O)\u2014NH\u2014R 7 , (CH 2 ) m \u2014SO 2 R 7 , O\u2014SO 2 R 7 , (CH 2 ) m \u2014C(O)R 7  and (CH 2 ) m \u2014C(O)NR 7 R 8 ; R 2 is selected from R 9 , CH 2 , \u2550CH\u2014(CH 2 ) m \u2014CH 3 , \u2550O, (CH 2 ) r \u2014OR 9 , (CH 2 ) r \u2014CO 2 R 9 , (CH 2 ) r \u2014NR 9 R 10 , O\u2014(CH 2 ) s \u2014NR 9 , R 10 , NH\u2014C(O)\u2014R 9 , O\u2014(CH 2 ) s \u2014NH\u2014C(O)\u2014R 9 , O\u2014(CH 2 ) s \u2014C(O)\u2014NH\u2014R 9 , (CH 2 ) r \u2014SO 2 R 9 , O\u2014SO 2 R 9 , (CH 2 ) r \u2014COR 9  and (CH 2 ) r \u2014C(O)NR 9 R 10 ; R 3  is selected from H, C 1-12  alkyl and CH 2 Ph; R 4  is selected from phenyl and C 5-9  heteroaryl groups optionally substituted with up to three optional substituent groups selected from OH, C 1-6  alkyl, OC 1-6  alkyl, (CH 2 ) j \u2014CO 2 R 11 , O\u2014(CH 2 ) k \u2014NR 11 R 12 , (CH 2 ) j \u2014NR 11 R 12 , C(\u2550O)\u2014NH\u2014(CH 2 ) k \u2014NR 11 R 12 ; C(\u2550O)\u2014NH\u2014R 24  and C(\u2550O)\u2014NH\u2014(CH 2 ) k \u2014C(\u2550NH)NR 11 R 12 ; with the proviso that the optionally substituted C 5-9  heteroaryl is not indolyl; R 19  is selected from H and (CH 2 ) t \u2014NR 20 R 21 ; Y 1  is N or CH; Y 2  is N or CH; and wherein at least one of Y 1  and Y 2  is CH; p is 0 or 1; j, m, r and t are independently selected from an integer from 0 to 6; k, n and s are independently selected from an integer from 1 to 6; X 1  is selected from O, S, NR 13 , CR 13 R 14 , CR 13 R 14 O, C(\u2550O), C(\u2550O)NR 13 , NR 13 C(\u2550O), O\u2014C(O) and C(O)\u2014O; L is selected from an amino acid, a peptide chain having from 2 to 6 amino acids, an alkylene chain containing from 1 to 12 carbon atoms which may contain one or more carbon-carbon double or triple bonds, a paraformaldehyde chain \u2014(OCH 2 ) 1-12 \u2014, a polyethylene glycol chain \u2014(OCH 2 CH 2 ) 1-6 \u2014, wherein the chain may be interrupted by one or more of O, S, NH, C 5-9  heteroarylene, phenylene, or a combination of the foregoing; X 2  is selected from O, S, NR 15 , CR 15 R 16 , CR 15 R 16 , C(\u2550O), C(\u2550O)NR 15 , NR 15 C(\u2550O), O\u2014C(O) and C(O)\u2014O or is absent; q is selected from 0, 1, 2, 3, 4, 5 and 6; A is selected from: for each A1 group one of Y 3  and Y 4  is independently selected from N\u2014R 17 , S and O; and the other of Y 3  and Y 4  is CH; and Y 5  is independently selected from CH, N, S and COH; for each A2 group one of Y 6  and Y 7  is independently selected from N and CH; and the other of Y 6  and Y 7  is CH; R 7  and R 9  are independently selected from H, C 1-12  alkyl; C 5-9  heteroaryl, C 6-15  heteroarylatkyl, phenyl and C 7-12  aralkyl groups; wherein the heteroaryl, heteroarylalkyl, phenyl and aralkyl groups are optionally substituted with up to three optional substituent groups selected from C 1-6  alkyl, OH, OC 1-6  alkyl; R 24  is a phenyl optionally substituted with up to three optional substituent groups selected from OH, C 1-6  alkyl, OC 1-6  alkyl, (CH 2 ) j -CO 2 R 11 , O\u2014(CH 2 ) k \u2014NR 11 R 12 , (CH 2 ) j \u2014NR 11 R 12 , C(\u2550O)\u2014NH\u2014(CH 2 ) k \u2014NR 11 R 12  and C(\u2550O)\u2014NH\u2014(CH 2 ) k \u2014C(\u2550NH)NR 11 R 12 ; R 8 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 20  and R 21  are independently selected from H and C 1-6  alkyl; and either:\n (i) R 5  and R 6  together form a double bond; \n (ii) R 5  is H and R 6  is OH; or \n (iii) R 5  is H and R 6  is OC 1-6  alkyl; \n with the proviso that when p is 0 and A is A1, then:\n (a) for at least one A1 group one of Y 3  and Y 4  is selected from S and O; or \n (b) for at least one A1 group Y 5  is S; or \n (c) R 4  is not pyrrolyl, imidazolyl, optionally substituted pyrrolyl or optionally substituted imidazolyl.

Metadata:
- Claim Count in Document: 74.0
- Percentile: 91.0
- Lexical Diversity: 2.71141
- Patent Class: 540.0
- Transitional Phrase Type: none
- Component Type: 0
- Foreign Priority: True
- Related Applications: ['16061295', '15579148', '15135352', '14604129', '14238415']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.703576656259387
- 35 USC 102 Novelty (BERT): 0.5621266778889156
- Combined Prediction Score: 0.6894316584223399
- Mean Citation Score: 375.996744
- Max Citation Score: 431.64725
- Similarity Product: 306.29317155706883

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