PATENT CLAIM ANALYSIS

Application Number: 15755475
Application Type: Utility
Filing Date: 2018-02
Publication Date: 2018-08
Patent Classification: ["514", "046000"]

Abstract:
The present invention relates novel 6-6 bicyclic aromatic ring substituted nucleoside analogues of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as PRMT5 inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

Claim (Index 1):
A compound of Formula (I) wherein R 1  represents hydrogen or \u2014C(\u2550O)\u2014C 1-4 alkyl; R 2  represents hydrogen or \u2014C(\u2550O)\u2014C 1-4 alkyl; Y represents \u2014O\u2014, \u2014CH 2 \u2014 or \u2014CF 2 \u2014; Z represents \u2014CH 2 \u2014, \u2014X\u2014CR 5a R 5b \u2014, \u2014CR 5c \u2550CR 5d \u2014, \u2014CR 5c R 5g \u2014CR 5f R 5h \u2014, or \u2014C\u2261C\u2014; and when Y represents \u2014CH 2 \u2014 or \u2014CF 2 \u2014, then Z can also represent \u2014O\u2014 or \u2014CR 5a R 5b \u2014X\u2014; R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g , and R 5h  each independently represent hydrogen or C 1-4 alkyl; X represents \u2014O\u2014, \u2014S\u2014, or \u2014NR 11 \u2014; R 11  represents hydrogen, C 1-4 alkyl, or C 1-4 alkyl substituted with one substituent selected from the group consisting of \u2014OH, \u2014O\u2014C 1-4 alkyl, R 12 , \u2014NH 2 , \u2014NH\u2014C 1-4 alkyl, and \u2014N(C 1-4 alkyl) 2 ; R 12  represents a 4-, 5-, 6- or 7-membered heterocyclic ring containing one nitrogen atom and optionally one oxygen atom; said 4-, 5-, 6- or 7-membered heterocyclic ring being attached to the remainder of the molecule via a ring nitrogen atom; Ar represents a 10-membered bicyclic aromatic ring system consisting of two fused 6-membered rings, wherein optionally 1 or 2 ring carbon atoms are replaced by a nitrogen atom; provided that when the nitrogen atom replaces one of the two fused carbon atoms, a carbonyl group is present in said bicyclic aromatic ring system; Ar is optionally substituted with one, two, three or four substituents each independently selected from the group consisting of halo, \u2014OH, \u2014NH 2 , \u2014NH\u2014C 1-4 alkyl, \u2014N(C 1-4 alkyl) 2 , \u2014NHR 10d , \u2014NR 10c R 10d , cyano, \u2014CF 3 , \u2014C(\u2550O)\u2014NH 2 , \u2014C(\u2550O)\u2014NH\u2014C 1-4 alkyl, \u2014C(\u2550O)\u2014C 1-4 alkyl, C 1-4 alkyloxy, \u2014C(\u2550O)\u2014O\u2014C 1-4 alkyl, C 3-6 cycloalkyl, \u2014O\u2014C 3-6 cycloalkyl, \u2014NH\u2014C 3-6 cycloalkyl, \u2014N(C 3-6 cycloalkyl) 2 , C 2-6 alkenyl, C 1-4 alkyl substituted with one C 1-4 alkyloxy, and C 1-4 alkyl optionally substituted with one \u2014NR 10a R 10b ; R 10a  and R 10b  each independently represent hydrogen or C 1-4 alkyl; R 10c  and R 10d  each independently represent C 3-6 cycloalkyl; R 13 ; R 14 ; C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, \u2014OH and \u2014O\u2014C 1-4 alkyl; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, \u2014OH and \u2014O\u2014C 1-4 alkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of C 3-6 cycloalkyl, R 13  and R 14 ; R 13  represents a 4- to 7-membered monocyclic aromatic ring containing one, two or three heteroatoms each independently selected from O, S, S(\u2550O) p  and N; or a 6- to 11-membered bicyclic fused aromatic ring containing one, two or three heteroatoms each independently selected from O, S, S(\u2550O) p  and N; said 4- to 7-membered monocyclic aromatic ring or 6- to 11-membered bicyclic fused aromatic ring is optionally substituted with one or two substituents selected from the group consisting of C 1-4 alkyl; p represents 1 or 2; R 14  represents phenyl optionally substituted with one, two or three substituents each independently selected from the group consisting of halo; Het represents a bicyclic aromatic heterocyclic ring system selected from the group consisting of (a-1), (a-2), (a-3), (a-4) and (a-5): R 3a , R 3b , R 3c , R 3d  and R 3e  each independently represent hydrogen, halo, \u2014NR 7a R 7b , C 1-4 alkyl, C 2-4 alkenyl, C 3-6 cycloalkyl, \u2014OH, or \u2014O\u2014C 1-4 alkyl; R 7a  represents hydrogen; R 7b  represents hydrogen, C 3-6 cycloalkyl, or C 1-4 alkyl; R 4a , R 4b , R 4c , R 4d , R 4e , R 4f  and R 4g  each independently represent hydrogen, halo, \u2014NR 8a R 8b , or C 1-4 alkyl; R 8a  and R 8b  each independently represent hydrogen or C 1-4 alkyl; Q 1  represents N or CR 6a ; Q 2  represents N or CR 6b ; Q 3  represents N or CR 6c ; Q 4  represents N or CR 6d ; provided that maximum one of Q 3  and Q 4  represents N; Q 8  represents N or CR 6g ; Q 9  represents N or CR 6h ; Q 10  represents N or CR 6i ; Q 11  represents N or CR 6j ; Q 5  represents CR 3d ; Q 6  represents N; and Q 7  represents CR 4f ; or Q 5  represents CR 3d ; Q 6  represents CR 4e ; and Q 7  represents N; or Q 5  represents N; Q 6  represents CR 4e ; and Q 7  represents CR 4f ; or Q 5  represents N; Q 6  represents CR 4e ; and Q 7  represents N; or Q 5  represents N; Q 6  represents N; and Q 7  represents CR 4f ; or Q 5  represents N; Q 6  represents N; and Q 7  represents N; R 6a , R 6b , R 6c , R 6d , R 6e , R 6f , R 6g , R 6h , R 6i  and R 6j  each independently represent hydrogen, halogen, C 1-4 alkyl, \u2014NR 9a R9b, or C 1-4 alkyl substituted with one, two or three halo atoms; R 9a  and R 9b  each independently represent hydrogen or C 1-4 alkyl; or a pharmaceutically acceptable addition salt or a solvate thereof; provided that the following compounds, and pharmaceutically acceptable addition salts, and solvates thereof are excluded:

Metadata:
- Claim Count in Document: 35.0
- Percentile: 88.0
- Lexical Diversity: 1.45652
- Patent Class: 514.0
- Transitional Phrase Type: closed
- Component Type: 1
- Foreign Priority: True
- Related Applications: ['13207696', '16331579', '15502884', '14619371', '13983248']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7732627530892825
- 35 USC 102 Novelty (BERT): 0.5235814885997309
- Combined Prediction Score: 0.7482946266403274
- Mean Citation Score: 301.543934
- Max Citation Score: 304.53442
- Similarity Product: 208.01994298165084

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

Dataset: test