PATENT CLAIM ANALYSIS

Application Number: 16033636
Application Type: Utility
Filing Date: 2018-07
Publication Date: 2020-01
Patent Classification: ["514", "210180"]

Abstract:
Compounds of structural Formula I were developed for the treatment of infections by filoviruses including Ebolavirus and Marburgvirus, wherein, R 1 , R 2 , R 3 , X and Y are defined in the specification.

Claim (Index 37):
A method of treating infections associated with viruses of the Filoviridae enveloped virus, or any virus expressing filovirus glycoproteins to mediate cell entry comprising administration of a therapeutically effective amount of a compound of Structural Formula I or a pharmaceutically acceptable salt, and a pharmaceutically acceptable carrier, diluent, or vehicle thereof, wherein: X is C-A-D, and Y is a bond or CR 4 R 5 ; or X is CR 5  and Y is CR 4 -A-D; A is \u2014C(R 6a R 6b ) j \u2014, (C 6  to C 10 ) arylene, or (C 2  to C 9 ) heteroarylene, wherein each of the said (C 6  to C 10 ) arylene or (C 2  to C 9 ) heteroarylene is optionally substituted with at least one R 6a  group; D is selected from the group consisting of wherein R 10b  is selected from the group consisting of R 1  is selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a R 11b , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n CO)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and \u2014NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; R 2  is selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a R 11b ), (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n C(O)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; R 3  is selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a R 11b ), (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 5  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n C(O)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; R 4  is selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a R 11b , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n C(O)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; R 5  is selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a  S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n C(O)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and \u2014NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; each of the R 6a  and R 6b  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a R 11b , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n C(O)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and \u2014NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; each R 8  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene is optionally substituted with at least one R 13  group; each of the R 9a , R 9b , and R 9c  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 11a R 11b , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, \u2014C(O)R 12 , \u2014C(O)NR 11a R 11b , \u2014S(O) m R 12 , \u2014S(O) m NR 11a R 11b , \u2014NR 11a S(O) m R 12 , \u2014(CH 2 ) n C(O)OR 12 , \u2014(CH 2 ) n C(O)N(R 11a R 11b ), \u2014(CH 2 ) n N(R 11a R 11b ), \u2014OC(O)R 12 , \u2014NR 11a C(O)R 12 , and \u2014NR 11a C(O)N(R 11a R 11b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; each of the R 11a  and R 11b  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene is optionally substituted with at least one R 13  group, or R 11a  and R 11b  may be taken together with the nitrogen atom to which they are attached to form a (C 2  to C 10 ) cycloheteroalkyl ring, wherein said (C 2  to C 10 ) cycloheteroalkyl ring has 1 to 3 ring heteroatoms selected from the group consisting of N, O, and S, and wherein the said (C 2  to C 10 ) cycloheteroalkyl ring is optionally substituted with at least one R 13  group; each of the R 12  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 3  to C 10 ) cycloalkyl, (C 6  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 5  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 5  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 13  group; each R 13  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 14a R 14b , oxo, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, (C 2  to C 10 ) cycloheteroalkylene, \u2014C(O)R 15 , \u2014C(O)NR 14a R 14b , \u2014S(O) m R 15 , \u2014S(O) m NR 14a R 14b , \u2014NR 14a S(O) m R 15 , \u2014(CH 2 ) n C(O)OR 15 , \u2014(CH 2 ) n C(O)N(R 14a R 14b ), (CH 2 ) n N(R 14a R 14b )OC(O)R 15 , \u2014O(CH 2 ) n O\u2014, \u2014NR 14a C(O)R 15 , and \u2014NR 14a C(O)N(R 14a R 14b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 5  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, and (C 2  to C 10 ) cycloheteroalkylene is optionally substituted with at least one R 16  group; each of the R 14a  and R 14b  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 9 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene is optionally substituted with at least one R 16  group, or R 14a  and R 14b  may be taken together with the nitrogen atom to which they are attached to form a (C 2  to C 10 ) cycloheteroalkyl ring, wherein said (C 2  to C 10 ) cycloheteroalkyl ring has 1 to 3 ring heteroatoms selected from the group consisting of N, O, and S, and wherein the said (C 2  to C 10 ) cycloheteroalkyl ring is optionally substituted with at least one R 16  group; each R 15  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 16  group; each R 16  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 17a R 17b , oxo, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, (C 2  to C 10 ) cycloheteroalkylene, \u2014C(O)R 18 , \u2014C(O)NR 17a R 17b , \u2014S(O) m R 18 , \u2014S(O) m NR 17a R 17b , \u2014NR 17a S(O) m R 18 , \u2014(CH 2 ) n C(O)OR 18 , \u2014(CH 2 ) n C(O)N(R 17a R 17b ), \u2014(CH 2 ) n N(R 17a R 17b ), \u2014OC(O)R 18 , \u2014NR 17a C(O)R 18 , and \u2014NR 17a C(O)N(R 17a R 17b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) aryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, and (C 2  to C 10 ) cycloheteroalkylene is optionally substituted with at least one R 19  group; each of the R 17a  and R 17b  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, and (C 2  to C 9 ) heteroarylene is optionally substituted with at least one R 19  group, or R 17a  and R 17b  may be taken together with the nitrogen atom to which they are attached to form a (C 2  to C 10 ) cycloheteroalkyl ring, wherein said (C 2  to C 10 ) cycloheteroalkyl ring has 1 to 3 ring heteroatoms selected from the group consisting of N, O, and S, and wherein the said (C 2  to C 10 ) cycloheteroalkyl ring is optionally substituted with at least one R 19  group; each R 18  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 2  to C 9 ) heteroaryl, and (C 6  to C 10 ) aryl is optionally substituted with at least one R 19  group; each R 19  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 20a R 20b , oxo, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, (C 2  to C 10 ) cycloheteroalkylene, \u2014C(O)R 21 , \u2014C(O)NR 20a R 20b , \u2014S(O) m R 21 , \u2014S(O) m NR 20a R 20b , NR 20a S(O) m R 21 , \u2014(CH 2 ) n C(O)OR 21 , \u2014(CH 2 ) n C(O)N(R 20a R 20b ), \u2014(CH 2 ) n N(R 20a R 20b ), \u2014OC(O)R 21 , \u2014NR 20a C(O)R 21 , and \u2014NR 20a C(O)N(R 20a R 20b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, and (C 2  to C 10 ) cycloheteroalkylene is optionally substituted with at least one R 22  group; each of the R 20a  and R 20b1  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl, wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl is optionally substituted with at least one R 22  group, or R 20a  and R 20b  may be taken together with the nitrogen atom to which they are attached to form a (C 2  to C 10 ) cycloheteroalkyl ring, wherein said (C 2  to C 10 ) cycloheteroalkyl ring has 1 to 3 ring heteroatoms selected from the group consisting of N, O, and S, and wherein the said (C 2  to C 10 ) cycloheteroalkyl ring is optionally substituted with at least one R 22  group; each R 21  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl; each R 22  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 23a R 23b , oxo, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, (C 2  to C 10 ) cycloheteroalkylene, \u2014C(O)R 24 , \u2014C(O)NR 23a R 23b , \u2014S(O) m R 24 , \u2014S(O) m NR 23a R 23b , \u2014NR 23a S(O) m R 24 , \u2014(CH 2 ) n C(O)OR 24 , \u2014(CH 2 ) n C(O)N(R 23a R 23b ), \u2014(CH 2 ) n N(R 23a R 23b ), \u2014OC(O)R 24 , \u2014NR 23a C(O)R 24 , and \u2014NR 23a C(O)N(R 23a R 23b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, and (C 2  to C 10 ) cycloheteroalkylene is optionally substituted with at least one R 25  group; each of the R 23a  and R 23b  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 2  to C 9 ) heteroaryl, and (C 6  to C 10 ) aryl; each R 24  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl; each R 25  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , \u2014NR 26a R 26b , oxo, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, (C 2  to C 10 ) cycloheteroalkylene, \u2014C(O)R 27 , \u2014C(O)NR 26a R 26b , \u2014S(O) m R 27 , \u2014S(O) m NR 26a R 26b , \u2014NR 26a S(O) m R 27 , \u2014(CH 2 ) n C(O)OR 27 , \u2014(CH 2 ) n C(O)N(R 26a R 26b ), \u2014(CH 2 ) n N(R 26a R 26b ), \u2014OC(O)R 27 , \u2014NR 26a C(O)R 27 , and \u2014NR 26a C(O)N(R 26a R 26b ), wherein each of the said (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, (C 2  to C 9 ) heteroaryl, (C 6  to C 10 ) arylene, (C 2  to C 9 ) heteroarylene, (C 3  to C 10 ) cycloalkylene, and (C 2  to C 10 ) cycloheteroalkylene is optionally substituted with at least one R 27  group; each of the R 26a  and R 26b  is independently selected from hydrogen, (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl, or R 26a  and R 26b  may be taken together with the nitrogen atom to which they are attached to form a (C 2  to C 10 ) cycloheteroalkyl ring, wherein said (C 2  to C 10 ) cycloheteroalkyl ring has 1 to 3 ring heteroatoms selected from the group consisting of N, O, and S; each R 27  is independently selected from hydrogen, halogen, OH, nitro, CF 3 , (C 1  to C 10 ) alkyl, (C 1  to C 10 ) alkenyl, (C 1  to C 10 ) alkynyl, (C 1  to C 10 ) alkoxy, aryloxy, cyano, (C 3  to C 10 ) cycloalkyl, (C 5  to C 10 ) cycloalkenyl, (C 2  to C 10 ) cycloheteroalkyl, (C 6  to C 10 ) aryl, and (C 2  to C 9 ) heteroaryl; h is 1 or 2; i is 2, 3, 4, 5, or 6; j is 0, 1, 2, 3, 4, or 5; k is 1, 2, 3, 4, or 5; m is 0, 1 or 2; n is 0, 1, 2, 3, or 4; with the proviso that when X is C-A-D, and Y is CH 2 , then R 1  is not selected from the group consisting of hydrogen and methyl, and with the proviso that the following compounds shall be excluded:

Metadata:
- Claim Count in Document: 2.0
- Percentile: 95.0
- Lexical Diversity: 1.3
- Patent Class: 514.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: False
- Related Applications: ['12702937', '13091895', '09669298', '11034635', '13121900']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7833575614499027
- 35 USC 102 Novelty (BERT): 0.5721594491247814
- Combined Prediction Score: 0.7622377502173906
- Mean Citation Score: 332.16656
- Max Citation Score: 360.32703
- Similarity Product: 212.3880460995144

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