throbber
Summary of FAAs in Kohn References
`
`
`R2
`
`CH3
`
`CH3
`
`CH3
`
`H
`CH(CH3)2
`Ph
`
`Ph
`
`Ph
`
`CH2CH2SCH3
`
`R1
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`CH3
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`
`
`R3
`
`H
`
`H
`
`H
`
`H
`H
`H
`
`H
`
`H
`
`H
`
`R4
`
`Bn
`
`Bn
`
`Bn
`
`Bn
`Bn
`Bn
`
`Bn
`
`Bn
`
`Bn
`
`
`
`1
`
`
`
`n α
`
`Reference/Compound
`No.
`0 R,S Conley 1987 (1a)
`Kohn 1988 (D,L-AAB)
`Kohn 1990 (2a)
`Kohn 1991 (2a)
`Kohn 1993 (50)
`Kohn 1988 (D-AAB)
`Kohn 1990 ((R)-2a)
`Kohn 1988 (L-AAB)
`Kohn 1990 ((S)-2a)
`0 R,S Conley 1987 (1b)
`0 R,S Conley 1987 (1c)
`0 R,S Conley 1987 (1d)
`Kohn 1988 (D,L-APB)
`Kohn 1990 (2b)
`Kohn 1991 (2b)
`Kohn 1993 (3)
`Bardel 1994 (10)
`Kohn 1988 (D-APB)
`Kohn 1990 ((R)-2b)
`Kohn 1988 (L-APB)
`Kohn 1990 ((S)-2b)
`0 R,S Conley 1987 (1e)
`
`0 R
`
`0 S
`
`0 R
`
`0 S
`
`ED50
`
`76.54
`
`TD50
`
`453.86
`
`54.8
`
`548
`
`
`
`32.1
`
`214
`
`841
`
`
`
`>40
`
`26.4
`
`>300
`
`
`
`>80
`
`>100,
`<300
`
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 1/7
`
`

`
`R1
`
`R2
`
`Bn
`CH3
`Ph
`CH3
`H
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`(CH3)2CH
`CH3
`(CH3)3C
`CH3CONHCH2 CH3
`Bn
`CH3
`Bn
`Ph
`CH3
`2-Furanyl
`
`2-Furanyl
`
`2-Furanyl
`
`2-Pyrrolyl
`
`2-Thienyl
`
`3-Thienyl
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`
`
`R3
`
`H
`Ph
`H
`H
`H
`H
`H
`H
`H
`H
`H
`H
`H
`H
`H
`
`H
`
`H
`
`H
`
`H
`
`H
`
`R4
`
`Bn
`Bn
`Bn
`Bn
`CH3
`CH(Ph)2
`m-OCH3-Bn
`m-F-Bn
`CH2CONH-Bn
`Bn
`Bn
`Bn
`CH3
`CH3
`Bn
`
`Bn
`
`Bn
`
`Bn
`
`Bn
`
`Bn
`
`2
`
`n α
`
`Reference/Compound
`No.
`0 R,S Conley 1987 (1f)
`0 R,S Conley 1987 (1g)
`1 R,S Conley 1987 (1h)
`1 R,S Conley 1987 (1i)
`0 R,S Conley 1987 (1j)
`0 R,S Conley 1987 (1k)
`0 R,S Conley 1987 (1l)
`0 R,S Conley 1987 (1m)
`0 R,S Conley 1987 (1n)
`0 R,S Conley 1987 (1o)
`0 R,S Conley 1987 (1p)
`0 R,S Conley 1987 (1q)
`0 R,S Conley 1987 (1r)
`0 R,S Conley 1987 (1s)
`0 R,S Kohn 1990 (2g)
`Kohn 1991 (2d)
`Kohn 1993 (4)
`Bardel 1994 (2)
`Kohn 1990 ((R)-2g)
`Kohn 1993 ((R)-4)
`Kohn 1990 ((S)-2g)
`Kohn 1993 ((S)-4)
`0 R,S Kohn 1990 (2i)
`Kohn 1991 (2c)
`Kohn 1993 (5)
`Bardel 1994 (3)
`0 R,S Kohn 1990 (2l)
`Kohn 1993 (7)
`Bardel 1994 (4)
`0 R,S Kohn 1990 (2m)
`Kohn 1993 (8)
`
`0 R
`
`0 S
`
`ED50
`
`
`
`
`
`
`
`
`77.38
`
`
`
`
`
`
`10.3
`
`3.3
`
`>25
`
`16.1
`
`44.8
`
`87.8
`
`TD50
`
`
`
`
`
`
`
`
`142.73
`
`
`
`
`
`
`~40
`
`23.8
`
`>200
`
`>30,
`<100
`
`>30,
`<100
`
`>100
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 2/7
`
`

`
`R1
`
`CH3
`CH3
`
`CH3
`CH3
`
`CH3
`
`CH3
`
`CH3
`CH3
`CH3
`
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`
`CH3
`CH3
`CH3
`
`CH3
`CH3
`
`CH3
`CH3
`
`
`
`R2
`
`R3
`
`R4
`
`β-Naphthyl
`2-Benzo[b]furanyl
`
`3-Indolyl
`2-Benzo[b]thienyl
`
`OCH3
`
`OCH2CH3
`
`CN
`CONH2
`CH2OH
`
`4-OH-Ph
`4-OCH3-Ph
`2-OH-5-CH3-Ph
`5-CH3-2-furanyl
`5-CH3-2-pyrrolyl
`1-CH3-2-pyrrolyl
`
`2-Furanyl
`2-Furanyl
`2-Furanyl
`
`2-Furanyl
`2-Furanyl
`
`2-Furanyl
`2-Furanyl
`
`H
`H
`
`H
`H
`
`H
`
`H
`
`H
`H
`H
`
`H
`H
`H
`H
`H
`H
`
`H
`H
`H
`
`H
`H
`
`H
`H
`
`Bn
`Bn
`
`Bn
`Bn
`
`Bn
`
`Bn
`
`Bn
`Bn
`Bn
`
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`
`2-F-Bn
`3-F-Bn
`4-F-Bn
`
`2,5-F-Bn
`2,6-F-Bn
`
`(R)-α-CH3-Bn
`(R)-α-CH3-Bn
`3
`
`n α
`
`Reference/Compound
`No.
`Bardel 1994 (5)
`0 R,S Kohn 1990 (2f)
`0 R,S Kohn 1990 (2n)
`
`0 R,S Kohn 1990 (2o)
`0 R,S Kohn 1990 (2p)
`
`0 R,S Kohn 1991 (3s)
`
`0 R,S Kohn 1990 (5)
`Kohn 1991 (3t)
`0 R,S Kohn 1993 (34)
`0 R,S Kohn 1993 (41)
`0 R,S Kohn 1993 (49)
`
`0 R,S Kohn 1990 (2c)
`0 R,S Kohn 1990 (2d)
`0 R,S Kohn 1990 (2e)
`0 R,S Kohn 1990 (2h)
`0 R,S Kohn 1990 (2j)
`0 R,S Kohn 1990 (2k)
`Kohn 1993 (6)
`0 R,S Kohn 1990 (3a)
`0 R,S Kohn 1990 (3b)
`0 R,S Kohn 1990 (3c)
`Kohn 1993 (30)
`0 R,S Kohn 1990 (3d)
`0 R,S Kohn 1990 (3e)
`
`0 S
`0 R
`
`Kohn 1990 (4a)
`Kohn 1990 (4b)
`
`ED50
`
`TD50
`
`>300
`>100,
`<300
`>300
`>100,
`<300
`98.3
`
`62.0
`
`>300
`>300
`>100,
`<300
`>300
`>300
`>300
`19.2
`36.5
`~300
`
`40.0
`13.3
`12.7
`
`23.8
`>25,
`<100
`
`
`
`>300
`>100,
`<300
`<300
`>100,
`<300
`>100,
`<300
`>112
`
`>300
`>300
`<300
`
`na
`na
`na
`75.4
`na
`na
`
`na
`136
`144
`
`na
`na
`
`
`
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 3/7
`
`

`
`R2
`
`2-Furanyl
`2-Furanyl
`NH2
`
`NHCH3
`NHCH2CH3
`
`N(CH3)2
`N-morpholino
`
`N+(CH3)3 BF4
`
`-
`
`NHPh
`3-pyrazolylamino
`NHC(O)CH3
`
`NHC(O)CF3
`
`NHOH
`NH(OCH3)
`
`N(CH3)OH
`N(CH3)OCH3
`
`N-Isoxazolidino
`
`NHNHPh
`NHNHCO2CH2Ph
`
`OH
`
`R1
`
`CH3
`CH3
`CH3
`
`CH3
`CH3
`
`CH3
`CH3
`
`CH3
`
`CH3
`CH3
`CH3
`
`CH3
`
`CH3
`CH3
`
`CH3
`CH3
`
`CH3
`
`CH3
`CH3
`
`CH3
`
`
`
`R3
`
`R4
`
`H
`H
`H
`
`H
`H
`
`H
`H
`
`H
`
`H
`H
`H
`
`H
`
`H
`H
`
`H
`H
`
`H
`
`H
`H
`
`H
`
`(S)-α-CH3-Bn
`(S)-α-CH3-Bn
`Bn
`
`Bn
`Bn
`
`Bn
`Bn
`
`Bn
`
`Bn
`Bn
`Bn
`
`Bn
`
`Bn
`Bn
`
`Bn
`Bn
`
`Bn
`
`Bn
`Bn
`
`Bn
`
`4
`
`n α
`
`Reference/Compound
`No.
`Kohn 1990 (4c)
`0 R
`Kohn 1990 (4d)
`0 S
`0 R,S Kohn 1991 (3a)
`Kohn 1994 (2s)
`0 R,S Kohn 1991 (3b)
`0 R,S Kohn 1991 (3c)
`Kohn 1994 (2a)
`0 R,S Kohn 1991 (3d)
`0 R,S Kohn 1991 (3e)
`
`0 R,S Kohn 1991 (3f)
`Kohn 1994 (2u)
`0 R,S Kohn 1991 (3g)
`0 R,S Kohn 1991 (3h)
`0 R,S Kohn 1991 (3i)
`Kohn 1994 (2v)
`0 R,S Kohn 1991 (3j)
`Kohn 1994 (2w)
`0 R,S Kohn 1991 (3k)
`0 R,S Kohn 1991 (3l)
`Kohn 1994 (2c)
`Bardel 1994 (24)
`0 R,S Kohn 1991 (3m)
`0 R,S Kohn 1991 (3n)
`Kohn 1994 (2d)
`0 R,S Kohn 1991 (3o)
`Bardel 1994 (25)
`0 R,S Kohn 1991 (3p)
`0 R,S Kohn 1991 (3q)
`Kohn 1994 (2b)
`0 R,S Kohn 1991 (3r)
`
`ED50
`
`TD50
`
`
`
`65.1
`
`44.5
`42.4
`
`45.3
`>30,
`<100
`>100
`
`>300
`~100
`>100,
`<300
`>300
`
`~100
`6.2
`
`~30
`6.7
`
`31.4
`
`~100
`55.6
`
`80.1
`
`
`
`na
`
`na
`na
`
`na
`na
`
`na
`
`na
`na
`na
`
`na
`
`
`46.0
`
`na
`50.5
`
`na
`
`na
`na
`
`na
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 4/7
`
`

`
`R1
`
`CH3
`CH3
`
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`
`CH3
`
`CH3
`CH3
`
`CH3
`CH3
`CH3
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`CH3
`CH3
`
`
`
`R2
`
`OPh
`SCH2CH3
`
`SCH3
`SPh
`S(O)CH2CH3
`S(O)CH2CH3
`S(O2)CH2CH3
`2-imidazolyl
`
`5-imidazolyl
`
`5-(1H-1,2,4)-triazolyl
`5-tetrazolyl
`
`1-pyrrolyl
`1-pyrazolyl
`1-imidazolyl
`1-(1,2,4)-triazolyl
`
`1-tetrazolyl
`
`2-oxazolyl
`
`2-thiozolyl
`
`3-(1,2,4-oxadiazolyl)
`
`2-tetrahydrofuranyl
`2-furanyl
`2-furanyl
`
`R3
`
`H
`H
`
`H
`H
`H
`H
`H
`H
`
`H
`
`H
`H
`
`H
`H
`H
`H
`
`H
`
`H
`
`H
`
`H
`
`R4
`
`Bn
`Bn
`
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`
`Bn
`
`Bn
`Bn
`
`Bn
`Bn
`Bn
`Bn
`
`Bn
`
`Bn
`
`Bn
`
`Bn
`
`Bn
`H
`CH3 Bn
`H
`Bn (amide)
`5
`
`n α
`
`Reference/Compound
`No.
`0 R,S Kohn 1991 (3u)
`0 R,S Kohn 1991 (3w)
`
`0 R,S Kohn 1991 (3v)
`0 R,S Kohn 1991 (3x)
`0 R,S Kohn 1991 (3y-1)
`0 R,S Kohn 1991 (3y-mix)
`0 R,S Kohn 1991 (3z)
`0 R,S Kohn 1993 (9)
`Bardel 1994 (7)
`0 R,S Kohn 1993 (10)
`Bardel 1994 (8)
`0 R,S Kohn 1993 (11)
`0 R,S Kohn 1993 (12)
`
`0 R,S Kohn 1993 (13)
`0 R,S Kohn 1993 (14)
`0 R,S Kohn 1993 (15)
`0 R,S Kohn 1993 (16)
`
`0 R,S Kohn 1993 (17)
`
`0 R,S Kohn 1993 (18)
`Bardel 1994 (6)
`0 R,S Kohn 1993 (19)
`Bardel 1994 (9)
`0 R,S Kohn 1993 (20)
`
`0 R,S Kohn 1993 (21a-b)
`0 R,S Kohn 1993 (22)
`0 R,S Kohn 1993 (23)
`
`ED50
`
`>100
`>30,
`<100
`>100
`>300
`>100
`>100
`>100
`>100
`
`>100
`
`>100
`>30,
`<100
`80.2
`16.5
`>100
`>30,
`<100
`>300
`
`10.4
`
`12.1
`
`TD50
`
`na
`na
`
`na
`na
`na
`na
`na
`na
`
`na
`
`na
`na
`
`na
`na
`na
`na
`
`na
`
`38.6
`
`69.1
`
`na
`
`>100,
`<100
`51.7/89.8 na
`>300
`na
`18.4
`na
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 5/7
`
`

`
`R1
`
`R2
`
`R3
`
`R4
`
`n α
`
`Reference/Compound
`No.
`
`ED50
`
`TD50
`
`2-furanyl
`
`2-furanyl
`
`2-furanyl
`
`2-furanyl
`
`2-furanyl
`
`2-furanyl
`
`2-furanyl
`2-furanyl
`2-furanyl
`2-furanyl
`CH3
`
`(thioamide)
`CH3
`(thioamide)
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`
`CH3
`CH3
`CH3
`CH3
`CH3
`
`CH3
`
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`
`
`
`2-pyridinyl
`
`2-pyrazinyl
`2-pyrimidinyl
`NHC(O)OCH3
`NHC(O)OPh
`NHC(O)NHCH3
`NHC(O)NHPh
`NHC(O)NHS(O2)Ph
`NHC(S)NHCH3
`NHC(S)NHPh
`
`H
`
`H
`H
`H
`H
`H
`H
`H
`H
`H
`
`Bn
`
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`
`6
`
`H
`
`Bn (thioamide)
`
`0 R,S Kohn 1993 (24)
`
`H
`
`H
`
`H
`
`H
`
`H
`
`3-
`pyridinylmethyl
`4-
`pyridinylmethyl
`N-oxo-3-
`pyridinylmethyl
`N-oxo-4-
`pyridinylmethyl
`-N-oxide
`2-
`pyridinylamino
`4-F-Bn
`H
`4-F-Bn
`H
`4-CH3-Bn
`H
`4-CF3-Bn
`H
`CH3 Bn
`
`0 R,S Kohn 1993 (25)
`
`0 R,S Kohn 1993 (26)
`
`0 R,S Kohn 1993 (27)
`
`0 R,S Kohn 1993 (28)
`
`0 R,S Kohn 1993 (29)
`
`0 R,S Kohn 1993 (30)
`0 R
`Kohn 1993 (R-30)
`0 R
`Kohn 1993 (R-31)
`0 R
`Kohn 1993 (R-32)
`0 R,S Kohn 1993 (51)
`
`0 R,S Bardel 1994 (11)
`
`0 R,S Bardel 1994 (12)
`0 R,S Bardel 1994 (13)
`0 R,S Kohn 1994 (2e)
`0 R,S Kohn 1994 (2f)
`0 R,S Kohn 1994 (2g)
`0 R,S Kohn 1994 (2h)
`0 R,S Kohn 1994 (2i)
`0 R,S Kohn 1994 (2j)
`0 R,S Kohn 1994 (2k)
`
`>100
`
`~30
`
`>100
`
`~30
`
`>100
`
`>100
`
`12.7
`3.5
`43.6
`22.8
`>40,
`<100
`10.8
`
`14.8
`8.1
`48.0
`>100
`>100
`>100
`>100
`>100
`>100
`
`na
`
`na
`
`na
`
`na
`
`na
`
`na
`
`144
`14.4
`na
`na
`na
`
`>25,
`<100
`58.2
`56.7
`na
`na
`na
`na
`na
`na
`na
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 6/7
`
`

`
`R1
`
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`CH3
`
`CH3
`
`CH3
`CH3
`
`
`
`
`R2
`
`R3
`
`H
`NHC(O)Ph (2’-CO2H)
`H
`N-succinimidyl
`NHC(O)CH2NHC(O)OCH2Ph H
`H
`NHCH2C(O)OCH3
`NHCH2C(O)OCH2CH3
`H
`NHCH2C(O)OCH2Ph
`H
`-
`+NH2CH2CO2
`H
`Br
`H
`
`1-(dimethylsulfamoyl)imidazol-
`4-yl
`C(S)NH2
`C(NOH)NH2
`
`H
`
`H
`H
`
`R4
`
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`Bn
`
`Bn
`
`Bn
`Bn
`
`n α
`
`Reference/Compound
`No.
`0 R,S Kohn 1994 (2l)
`0 R,S Kohn 1994 (2m)
`0 R,S Kohn 1994 (2n)
`0 R,S Kohn 1994 (2o)
`0 R,S Kohn 1994 (2p)
`0 R,S Kohn 1994 (2q)
`0 R,S Kohn 1994 (2r)
`0 R,S Kohn 1993 (33)
`Kohn 1994 (2t)
`Bardel 1994 (14)
`0 R,S Kohn 1993 (37)
`
`0 R,S Kohn 1993 (42)
`0 R,S Kohn 1993 (43)
`
`ED50
`
`>100
`>100
`~30
`>100
`>100
`>100
`>100
`
`
`
`
`
`
`
`TD50
`
`na
`na
`na
`na
`na
`na
`na
`
`
`
`
`
`
`
`7
`
`Argentum Pharm. v. Research Corp. Techs., IPR2016-00204
`RCT EX. 2172 - 7/7

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