Granted Patent
B2
US 12,240,813 · App. 17/999,310 · Granted Mar 4, 2025
Deuterated tryptamine derivatives and methods of use
Assignee:
Cybin IRL Limited
View Patent ↗
Loading inventors, assignments & file history…
Abstract
The present disclosure is directed to chemical compounds and to the use of such compounds in the treatment of diseases associated with a serotonin 5-HT 2 receptor.
Claims (35)
1. A compound of Formula (I),
or an optically pure stereoisomer, pharmaceutically acceptable salt, solvate, or prodrug thereof,
wherein:
X 1 and X 2 are deuterium;
Y 1 and Y 2 are deuterium;
R is
R 2 is selected from hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted allyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
R 4 is hydrogen or deuterium;
R 5 is selected from hydrogen, deuterium, and unsubstituted or substituted alkoxy;
R 6 is selected from hydrogen, deuterium, and halogen;
R 7 is selected from hydrogen, deuterium, and halogen;
R 8 is an alkyl substituted with one or more deuterium;
R 9 is an alkyl substituted with one or more deuterium; and
R 10 is selected from hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted allyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl;
wherein at least one of R 6 and R 7 is halogen.
2. The compound of claim 1 , wherein R is
3. The compound of claim 1 , wherein R is
and R 10 is hydrogen.
4. The compound of claim 1 , wherein R 2 is hydrogen or deuterium.
5. The compound of claim 1 , wherein R 4 is hydrogen.
6. The compound of claim 1 , wherein R 5 is hydrogen.
7. The compound of claim 1 , wherein R 5 is deuterium.
8. The compound of claim 1 , wherein R 5 is unsubstituted alkoxy.
9. The compound of claim 8 , wherein R 5 is methoxy (MeO—).
10. The compound of claim 1 , wherein R 5 is alkoxy substituted with one or more deuterium.
11. The compound of claim 10 , wherein R 5 is fully deuterated methoxy (CD 3 O—).
12. The compound of claim 1 , wherein R 8 is methyl substituted with one or more deuterium.
13. The compound of claim 12 , wherein R 8 is fully deuterated methyl (—CD 3 ).
14. The compound of claim 1 , wherein R 9 is methyl substituted with one or more deuterium.
15. The compound of claim 14 , wherein R 9 is fully deuterated methyl (—CD 3 ).
16. The compound of claim 1 , wherein R 8 and R 9 are methyl substituted with one or more deuterium.
17. The compound of claim 16 , wherein R 8 and R 9 are fully deuterated methyl (—CD 3 ).
18. The compound of claim 1 , wherein R 6 is halogen.
19. The compound of claim 1 , wherein R 7 is halogen.
20. The compound of claim 1 , wherein both R 6 and R 7 are halogen.
Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 23, 2024
From: NIVOROZHKIN, ALEX
To: CYBIN CORP.
Reel/Frame 069664/0768 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 23, 2024
From: ADELIA THERAPEUTICS, INC.
To: CYBIN CORP.
Reel/Frame 069664/0796 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Nov 22, 2022
From: NIVOROZHKIN, ALEX; PALFREYMAN, MICHAEL
To: CYBIN IRL LIMITED
Reel/Frame 061848/0095 →
Continuity (4)
Provisional Application
63157118
· Mar 5, 2021
Provisional Application
63114738
· Nov 17, 2020
Provisional Application
63026939
· May 19, 2020
References Cited (400)
US 3072530A
· Albert et al.
· 1963
[cited by applicant]
US 3078214A
· Albert et al.
· 1963
[cited by applicant]
US 3192111A
· Hoffman et al.
· 1965
[cited by applicant]
US 3444174A
· Remers et al.
· 1969
[cited by applicant]
US 3686213A
· Poletto et al.
· 1972
[cited by applicant]
US 4855325A
· Naftchi
· 1989
[cited by applicant]
US 4861760A
· Mazuel et al.
· 1989
[cited by applicant]
US 4911920A
· Jani et al.
· 1990
[cited by applicant]
US 5158956A
· Gidda et al.
· 1992
[cited by applicant]
US 5212162A
· Missel et al.
· 1993
[cited by applicant]
US 5258379A
· Gidda et al.
· 1993
[cited by applicant]
US 5403841A
· Lang et al.
· 1995
[cited by applicant]
US 5417987A
· Dietz et al.
· 1995
[cited by applicant]
US 5594034A
· Gidda et al.
· 1997
[cited by applicant]
US 6107499A
· Shashoua
· 2000
[cited by applicant]
US 6207396B1
· Sigler
· 2001
[cited by applicant]
US 6306616B1
· Shindelman
· 2001
[cited by applicant]
US 6376531B1
· Bell
· 2002
[cited by applicant]
US 6403808B1
· Glennon et al.
· 2002
[cited by applicant]
US 6407137B2
· Shashoua
· 2002
[cited by applicant]
US 6815212B2
· Van Ness et al.
· 2004
[cited by applicant]
US 7052846B2
· Van Ness et al.
· 2006
[cited by applicant]
US 7642344B2
· Van Ness et al.
· 2010
[cited by applicant]
US 7745665B2
· Gant et al.
· 2010
[cited by applicant]
US 8980880B1
· King et al.
· 2015
[cited by applicant]
US 9139821B2
· Nazor et al.
· 2015
[cited by applicant]
US 9226925B1
· King et al.
· 2016
[cited by applicant]
US 9421266B2
· King et al.
· 2016
[cited by applicant]
US 9435816B2
· Johansen et al.
· 2016
[cited by applicant]
US 9458082B2
· Gant et al.
· 2016
[cited by applicant]
US 9775379B2
· Davidson et al.
· 2017
[cited by applicant]
US 9839241B2
· Davidson et al.
· 2017
[cited by applicant]
US 9974743B2
· Rose et al.
· 2018
[cited by applicant]
US 20010008641A1
· Krotzer
· 2001
[cited by applicant]
US 20030007961A1
· Wilburn
· 2003
[cited by applicant]
US 20030078231A1
· Wilburn
· 2003
[cited by applicant]
US 20030096013A1
· Werling et al.
· 2003
[cited by applicant]
US 20040105881A1
· Cevc et al.
· 2004
[cited by applicant]
US 20040258617A1
· Weber et al.
· 2004
[cited by applicant]
US 20050288616A1
· Bozenbury et al.
· 2005
[cited by applicant]
US 20060192098A1
· Danylewych-May
· 2006
[cited by applicant]
US 20080045588A1
· Gant et al.
· 2008
[cited by applicant]
US 20080010318A1
· Gant et al.
· 2008
[cited by applicant]
US 20080103189A1
· Gant et al.
· 2008
[cited by applicant]
US 20080220441A1
· Birnbaum et al.
· 2008
[cited by applicant]
US 20080227830A1
· Roberts et al.
· 2008
[cited by applicant]
US 20090028796A1
· Bednarek et al.
· 2009
[cited by applicant]
US 20090093513A1
· Hamann et al.
· 2009
[cited by applicant]
US 20090318527A1
· Sard et al.
· 2009
[cited by applicant]
US 20110060037A1
· Woldbye et al.
· 2011
[cited by applicant]
US 20110207627A1
· Liotta
· 2011
[cited by applicant]
US 20120108510A1
· Young
· 2012
[cited by applicant]
US 20120156139A1
· Katz-Brull
· 2012
[cited by applicant]
US 20120183600A1
· Chen
· 2012
[cited by applicant]
US 20130210167A1
· Benchikh et al.
· 2013
[cited by applicant]
US 20140066881A1
· Freeman
· 2014
[cited by applicant]
US 20140242722A1
· Knop et al.
· 2014
[cited by applicant]
US 20140349976A1
· Hacksell
· 2014
[cited by applicant]
US 20160067711A1
· Yoon et al.
· 2016
[cited by applicant]
US 20160250201A1
· Rose et al.
· 2016
[cited by applicant]
US 20160338945A1
· Knight
· 2016
[cited by applicant]
US 20170173262A1
· Veltz
· 2017
[cited by applicant]
US 20170210704A1
· Campbell
· 2017
[cited by applicant]
US 20170281652A1
· Altschul et al.
· 2017
[cited by applicant]
US 20180021326A1
· Stamets
· 2018
[cited by applicant]
US 20180147142A1
· Knight
· 2018
[cited by applicant]
US 20180343812A1
· Leo
· 2018
[cited by applicant]
US 20180354995A1
· Gudkov et al.
· 2018
[cited by applicant]
US 20190142851A1
· Chadeayne
· 2019
[cited by applicant]
US 20190246591A1
· Leo
· 2019
[cited by applicant]
US 20190254988A1
· Archibald
· 2019
[cited by applicant]
US 20200147038A1
· Russ et al.
· 2020
[cited by applicant]
US 20200172469A1
· Gant et al.
· 2020
[cited by applicant]
US 20200229411A1
· Leo
· 2020
[cited by applicant]
US 20200230128A1
· Bosse et al.
· 2020
[cited by applicant]
US 20200290992A1
· Zhang
· 2020
[cited by applicant]
US 20200375967A1
· Stamets
· 2020
[cited by applicant]
US 20210015738A1
· Larosa et al.
· 2021
[cited by applicant]
US 20210023052A1
· Chadeayne
· 2021
[cited by applicant]
US 20210030787A1
· Goren
· 2021
[cited by applicant]
US 20210069170A1
· Stamets
· 2021
[cited by applicant]
US 20210113644A1
· Chadeayne
· 2021
[cited by applicant]
US 20210137137A1
· Leo
· 2021
[cited by applicant]
US 20210137854A1
· Goren
· 2021
[cited by applicant]
US 20210183519A1
· Shlomi
· 2021
[cited by applicant]
US 20210236523A1
· Schindler et al.
· 2021
[cited by applicant]
US 20210267985A1
· Horn
· 2021
[cited by applicant]
US 20210322306A1
· Espinoza et al.
· 2021
[cited by applicant]
US 20210322447A1
· Plakogiannis
· 2021
[cited by applicant]
US 20220024956A1
· Slassi et al.
· 2022
[cited by applicant]
US 20220062237A1
· Layzell et al.
· 2022
[cited by applicant]
US 20220071958A1
· Terwey
· 2022
[cited by applicant]
US 20220105041A1
· Lubda et al.
· 2022
[cited by applicant]
US 20220110955A1
· Sippy
· 2022
[cited by applicant]
US 20220280482A1
· Barrow et al.
· 2022
[cited by applicant]
US 20220370413A1
· Barrow et al.
· 2022
[cited by applicant]
US 20230126298A1
· Nivorozhkin et al.
· 2023
[cited by applicant]
AT 501069T
· 2011
[cited by applicant]
AU 3230299A
· 1999
[cited by applicant]
AU 2007209313A1
· 2007
[cited by applicant]
AU 2009214724A1
· 2009
[cited by applicant]
AU 2014202047A1
· 2014
[cited by applicant]
AU 2018203524A1
· 2018
[cited by applicant]
AU 20210215274A1
· 2021
[cited by applicant]
CA 672478A
· 1963
[cited by applicant]
CA 2338326A1
· 2000
[cited by applicant]
CA 2422730A1
· 2002
[cited by applicant]
CA 2487849A1
· 2004
[cited by applicant]
CA 2489410A1
· 2004
[cited by applicant]
CA 2498938A1
· 2004
[cited by applicant]
CA 2686723A1
· 2008
[cited by applicant]
CA 2758774A1
· 2010
[cited by applicant]
CA 2796883A1
· 2011
[cited by applicant]
CA 2816595A1
· 2012
[cited by applicant]
CA 2838667A1
· 2012
[cited by applicant]
CA 2812063A1
· 2012
[cited by applicant]
CA 2909633A1
· 2014
[cited by applicant]
CA 2952818A1
· 2016
[cited by applicant]
CA 3050679A1
· 2018
[cited by applicant]
CA 3051914A1
· 2018
[cited by applicant]
CA 3052974A1
· 2018
[cited by applicant]
CA 3079560A1
· 2019
[cited by applicant]
CA 3099293A1
· 2019
[cited by applicant]
CA 3127854A1
· 2020
[cited by applicant]
CA 3088384A1
· 2020
[cited by applicant]
CN 1450065A
· 2003
[cited by applicant]
CN 1688288A
· 2005
[cited by applicant]
CN 101427140A
· 2009
[cited by applicant]
CN 101795621A
· 2010
[cited by applicant]
CN 102115455A
· 2011
[cited by applicant]
CN 102724913A
· 2012
[cited by applicant]
CN 103816150A
· 2014
[cited by applicant]
CN 204576485U
· 2015
[cited by applicant]
CN 105706423A
· 2016
[cited by applicant]
CN 105792942A
· 2016
[cited by applicant]
CN 106692144A
· 2017
[cited by applicant]
CN 107095680A
· 2017
[cited by applicant]
CN 107771056A
· 2018
[cited by applicant]
CN 107949314A
· 2018
[cited by applicant]
CN 108619214A
· 2018
[cited by applicant]
CN 108929259A
· 2018
[cited by applicant]
CN 109069073A
· 2018
[cited by applicant]
CN 109890371A
· 2019
[cited by applicant]
CN 110049723A
· 2019
[cited by applicant]
CN 110325954A
· 2019
[cited by applicant]
CN 209606445U
· 2019
[cited by applicant]
CN 110996775A
· 2020
[cited by applicant]
CN 112430187A
· 2021
[cited by applicant]
CS 276073B6
· 1992
[cited by applicant]
CZ 2015962A3
· 2017
[cited by applicant]
DE 255749A1
· 1988
[cited by applicant]
DE 265636A1
· 1989
[cited by applicant]
DE 102016014603A1
· 2018
[cited by applicant]
EP 0152379A2
· 1985
[cited by applicant]
EP 0850320A2
· 1998
[cited by applicant]
EP 0962464A2
· 1999
[cited by applicant]
EP 0990047A2
· 2000
[cited by applicant]
EP 1693366A1
· 2006
[cited by applicant]
EP 0992511B1
· 2009
[cited by applicant]
EP 3698260A1
· 2020
[cited by applicant]
EP 3713568A1
· 2020
[cited by applicant]
EP 3826632A1
· 2021
[cited by applicant]
EP 3844147A1
· 2021
[cited by applicant]
EP 3873883A1
· 2021
[cited by applicant]
ES 2355024A1
· 2011
[cited by applicant]
FI 34529A
· 1964
[cited by applicant]
FR 2448540A1
· 1980
[cited by applicant]
GB 672478
· 1952
[cited by applicant]
GB 912715
· 1959
[cited by applicant]
GB 911946A1
· 1962
[cited by applicant]
GB 912714A
· 1962
[cited by applicant]
GB 981192A
· 1965
[cited by applicant]
GB 982738A
· 1965
[cited by applicant]
GB 1264610A
· 1972
[cited by applicant]
GB 2586940A
· 2021
[cited by applicant]
GB 2588505A
· 2021
[cited by applicant]
GB 2585978B
· 2021
[cited by applicant]
GB 2592822A
· 2021
[cited by applicant]
GB 202107702A
· 2021
[cited by applicant]
GB 2595776A
· 2021
[cited by applicant]
GB 202106881A
· 2021
[cited by applicant]
HU 0400250A2
· 2004
[cited by applicant]
IN 201721041262A
· 2017
[cited by applicant]
JP H0827029A
· 1996
[cited by applicant]
JP 2005031029A
· 2005
[cited by applicant]
JP 2008183012A
· 2008
[cited by applicant]
JP 4786653B2
· 2011
[cited by applicant]
KR 20110028361A
· 2011
[cited by applicant]
KR 20110115128A
· 2011
[cited by applicant]
KR 20150046994A
· 2015
[cited by applicant]
MX 01005905A
· 2002
[cited by applicant]
PT 879054E
· 2008
[cited by applicant]
RU 2005101344A
· 2005
[cited by applicant]
RU 2005101343C2
· 2008
[cited by applicant]
SG 10201705968R
· 2017
[cited by applicant]
SG 10201707484U
· 2017
[cited by applicant]
TW 201103937A
· 2011
[cited by applicant]
TW 201242600A
· 2012
[cited by applicant]
TW 201605856A
· 2016
[cited by applicant]
TW 202045477A
· 2020
[cited by applicant]
TW 202103699A
· 2021
[cited by applicant]
TW 202128610A
· 2021
[cited by applicant]
WO 9101756A1
· 1991
[cited by applicant]
WO 9501334A1
· 1995
[cited by applicant]
WO 9826644A2
· 1998
[cited by applicant]
WO 9942840A1
· 1999
[cited by applicant]
WO 0003679A2
· 2000
[cited by applicant]
WO 0195903A1
· 2001
[cited by applicant]
WO 0205851A2
· 2002
[cited by applicant]
WO 0236113A1
· 2002
[cited by applicant]
WO 0236114A1
· 2002
[cited by applicant]
WO 02102988A2
· 2002
[cited by applicant]
WO 03016903A2
· 2003
[cited by applicant]
WO 2004025268A2
· 2004
[cited by applicant]
WO 2004054500A2
· 2004
[cited by applicant]
WO 2006086978A2
· 2006
[cited by applicant]
WO 2007024741A2
· 2007
[cited by applicant]
WO 2007097754A1
· 2007
[cited by applicant]
WO 2007110637A1
· 2007
[cited by applicant]
WO 2008003028A2
· 2008
[cited by applicant]
WO 2008016677A2
· 2008
[cited by applicant]
WO WO2008016677A3
· 2008
[cited by applicant]
WO 2008121610A1
· 2008
[cited by applicant]
WO 2008122990A1
· 2008
[cited by applicant]
WO 2008130638A2
· 2008
[cited by applicant]
WO 2009021055A1
· 2009
[cited by applicant]
WO 2009097596A1
· 2009
[cited by applicant]
WO 2009140680A1
· 2009
[cited by applicant]
WO 2010033724A2
· 2010
[cited by applicant]
WO 2010124089A2
· 2010
[cited by applicant]
WO 2010151258A1
· 2010
[cited by applicant]
WO 2011028875A1
· 2011
[cited by applicant]
WO 2011140607A1
· 2011
[cited by applicant]
WO 2011140608A1
· 2011
[cited by applicant]
WO 2012005951A1
· 2012
[cited by applicant]
WO 2012058337A2
· 2012
[cited by applicant]
WO 2012058769A1
· 2012
[cited by applicant]
WO 2012134436A1
· 2012
[cited by applicant]
WO 2012139042A2
· 2012
[cited by applicant]
WO 2013022775A1
· 2013
[cited by applicant]
WO 2013032940A1
· 2013
[cited by applicant]
WO 2013064690A1
· 2013
[cited by applicant]
WO 2014004460A1
· 2014
[cited by applicant]
WO 2014026044A2
· 2014
[cited by applicant]
WO 2014064703A1
· 2014
[cited by applicant]
WO 2014070424A1
· 2014
[cited by applicant]
WO 2014078374A
· 2014
[cited by applicant]
WO 2014144712A1
· 2014
[cited by applicant]
WO 2014146091A1
· 2014
[cited by applicant]
WO 2014152182A1
· 2014
[cited by applicant]
WO 2014152663A1
· 2014
[cited by applicant]
WO 2015066344A1
· 2015
[cited by applicant]
WO 2015073459A1
· 2015
[cited by applicant]
WO 2015073588A1
· 2015
[cited by applicant]
WO 2015090583A1
· 2015
[cited by applicant]
WO 2015094981A1
· 2015
[cited by applicant]
WO 2015122964A1
· 2015
[cited by applicant]
WO 2015127556A1
· 2015
[cited by applicant]
WO 2015127558A1
· 2015
[cited by applicant]
WO 2015164541A1
· 2015
[cited by applicant]
WO 2016033204A2
· 2016
[cited by applicant]
WO 2016057343A1
· 2016
[cited by applicant]
WO 2016138135A1
· 2016
[cited by applicant]
WO 2016161138A1
· 2016
[cited by applicant]
WO 2017044702A1
· 2017
[cited by applicant]
WO 2017112398A1
· 2017
[cited by applicant]
WO 2017189528A1
· 2017
[cited by applicant]
WO 2019018735A1
· 2018
[cited by applicant]
WO 2018031803A1
· 2018
[cited by applicant]
WO 2018049167A1
· 2018
[cited by applicant]
WO 2018057576A1
· 2018
[cited by applicant]
WO 2018064465A1
· 2018
[cited by applicant]
WO 2018089375A1
· 2018
[cited by applicant]
WO 2018106738A1
· 2018
[cited by applicant]
WO 2018135943A1
· 2018
[cited by applicant]
WO 2018136610A1
· 2018
[cited by applicant]
WO 2018145219A1
· 2018
[cited by applicant]
WO 2018148605A1
· 2018
[cited by applicant]
WO 2018195455A1
· 2018
[cited by applicant]
WO 2018204764A1
· 2018
[cited by applicant]
WO 2018207192A1
· 2018
[cited by applicant]
WO 2018223044A1
· 2018
[cited by applicant]
WO 2019021158A1
· 2019
[cited by applicant]
WO 2019058145A1
· 2019
[cited by applicant]
WO 2019073379A1
· 2019
[cited by applicant]
WO 2019079742A1
· 2019
[cited by applicant]
WO 2019081764A1
· 2019
[cited by applicant]
WO 2019099745A1
· 2019
[cited by applicant]
WO 2019109124A1
· 2019
[cited by applicant]
WO 2019122525A1
· 2019
[cited by applicant]
WO 2019173797A1
· 2019
[cited by applicant]
WO 2019241451A1
· 2019
[cited by applicant]
WO 2020023084A1
· 2020
[cited by applicant]
WO 2020219461A1
· 2020
[cited by applicant]
WO 2020024060A1
· 2020
[cited by applicant]
WO 2020024071A1
· 2020
[cited by applicant]
WO 2020041329A1
· 2020
[cited by applicant]
WO 2020053196A1
· 2020
[cited by applicant]
WO 2020058337A1
· 2020
[cited by applicant]
WO 2020148442A1
· 2020
[cited by applicant]
WO 2020157569A1
· 2020
[cited by applicant]
WO 2020169850A1
· 2020
[cited by applicant]
WO 2020169851A1
· 2020
[cited by applicant]
WO 20200157569A1
· 2020
[cited by applicant]
WO 2020176597A1
· 2020
[cited by applicant]
WO 2020181194A1
· 2020
[cited by applicant]
WO 2020185581A2
· 2020
[cited by applicant]
WO 2020212948A1
· 2020
[cited by applicant]
WO 2020212951A1
· 2020
[cited by applicant]
WO 2020245133A1
· 2020
[cited by applicant]
WO 2020247632A1
· 2020
[cited by applicant]
WO 2020260917A1
· 2020
[cited by applicant]
WO 2020264390A2
· 2020
[cited by applicant]
WO 2021000053A1
· 2021
[cited by applicant]
WO 2021000054A1
· 2021
[cited by applicant]
WO 2021000997A1
· 2021
[cited by applicant]
Cited By (1)