US 12,227,487 B1
Acyloxy substituted phenyl dithiane derivatives
Bishwajit Nag, Union City, CA (US); Ananda Sen, Castro Valley, CA (US); Nitish Nag, Union City, CA (US); Arjun Sanyal, Castro Valley, CA (US); and Srinivasan Narasimhan, Chennai (IN)
Assigned to RENOVEL INNOVATIONS, INC., Fremont, CA (US)
Filed by Renovel Innovations, Inc, Fremont, CA (US)
Filed on Sep. 18, 2023, as Appl. No. 18/469,323.
Application 18/469,323 is a continuation of application No. 17/499,684, filed on Oct. 12, 2021, granted, now 11,760,743.
Claims priority of provisional application 63/141,889, filed on Jan. 26, 2021.
Int. Cl. C07D 339/08 (2006.01); C07D 211/60 (2006.01); C07D 401/12 (2006.01); C07D 409/12 (2006.01)
CPC C07D 339/08 (2013.01) [C07D 211/60 (2013.01); C07D 401/12 (2013.01); C07D 409/12 (2013.01)] 3 Claims
 
1. A method for treating a disease in a subject, wherein the disease is associated with elevated levels of a bioactive compound selected from the group consisting of COX-1, COX2, TNF-α,
said method comprising administering to said subject an effective amount of a compound of formula (I)

OG Complex Work Unit Chemistry
wherein OOX may be present either at the ortho position or the para position with respect to the R1 group, wherein X is selected from the group consisting of alkanes, alkenes, alkynes, and aromatic or heterocyclic derivatives of an acid chloride, and wherein R1 is selected from the group consisting of a hydrogen, a halogen, a straight chain alkoxy group, and a branched alkoxy group, and pharmaceutically acceptable salts thereof, and further, wherein the compound comprises a structure selected from the group consisting of:
 
 
 
 IUPAC-OOX IUPAC-OOX
OOX R1 para to R1 ortho to R1
 
 

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 H 2-(1,3- dithian-2- yl)phenyl cinnamate 4-(1,3- dithian-2- yl)phenyl cinnamate
 
 

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 Cl 4-chloro-2- (1,3- dithian-2- yl)phenyl cinnamate 2-chloro-4- (1,3- dithian-2- yl)phenyl cinnamate
 
 

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 Br 4-bromo-2- (1,3- dithian-2- yl)phenyl cinnamate 2-bromo-4- (1,3- dithian-2- yl)phenyl cinnamate
 
 

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 OCH3 2-(1,3- dithian-2- yl)-4-methoxy- phenyl cinnamate 4-(1,3- dithian-2- yl)-2-methoxy- phenyl cinnamate
 
 

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 H (Z)-2-(1,3- dithian-2- yl)phenyl 3-(4-bromo- phenyl)- acrylate (E)-4-(1,3- dithian-2- yl)phenyl 3-(4-bromo- phenyl)- acrylate
 
 

OG Complex Work Unit Chemistry
 Cl (Z)-4-chloro-2-(1,3- dithian-2-yl)phenyl 3-(4-bromo- phenyl)- acrylate (E)-2-chloro- 4-(1,3- dithian-2- yl)phenyl 3-(4-bromo- phenyl)- acrylate
 
 

OG Complex Work Unit Chemistry
 Br (Z)-4-bromo- 2-(1,3- dithian-2-yl)phenyl 3-(4-bromo- phenyl)- acrylate (E)-2-bromo- 4-(1,3- dithian-2- yl)phenyl 3-(4-bromo- phenyl)- acrylate
 
 

OG Complex Work Unit Chemistry
 OCH3 (Z)-2-(1,3- dithian-2- yl)-4- methoxy- phenyl 3-(4-bromo- phenyl)- acrylate (E)-4-(1,3- dithian-2- yl)-2-methoxy- phenyl 3-(4-bromo- phenyl)- acrylate
 
 

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 H (Z)-2-(1,3- dithian-2- yl)phenyl 3- (pyridin- 4-yl)acrylate (E)-4-(1,3- dithian-2- yl)phenyl 3- (pyridin- 4-yl)acrylate
 
 

OG Complex Work Unit Chemistry
 Cl (Z)-4-chloro- 2-(1,3- dithian-2- yl)phenyl 3-(pyridin- 4-yl)acrylate (E)-2-chloro- 2-(1,3- dithian-2- yl)phenyl 3-(pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 Br (Z)-4-bromo- 2-(1,3- dithian-2- yl)phenyl 3-(pyridin- 4-yl)acrylate (E)-2-bromo- 2-(1,3- dithian-2- yl)phenyl 3-(pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 OCH3 (Z)-2-(1,3- dithian-2- yl)-4- methoxy- phenyl 3- (pyridin-4- yl)acrylate (E)-4-(1,3- dithian-2- yl)-4- methoxy phenyl 3- (pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 H (Z)-2-(1,3- dithian-2- yl)phenyl 3- (2-chloro- pyridin-4- yl)acrylate (E)-4-(1,3- dithian-2- yl)phenyl 3-(2-chloro- pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 Cl (Z)-4-chloro- 2-(1,3- dithian-2- yl)phenyl 3-(2-chloro- pyridin-4- yl)acrylate (E)-2-chloro- 2-(1,3- dithian-2- yl)phenyl 3-(2-chloro- pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 Br (Z)-4-bromo- 2-(1,3- dithian-2-yl)phenyl 3-(2-chloro- pyridin-4 yl)acrylate (E)-2-bromo- 2-(1,3- dithian-2- yl)phenyl 3-(2-chloro- pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 OCH3 (Z)-2-(1,3- dithian-2- yl)-4-methoxy- phenyl 3-(2-chloro- pyridin-4- yl)acrylate (E)-4-(1,3-dithian-2- yl)-4-methoxy- phenyl 3-(2- chloro- pyridin-4- yl)acrylate
 
 

OG Complex Work Unit Chemistry
 H (E)-2-(1,3- dithian-2- yl)phenyl hex-3- enoate (Z)-4-(1,3- dithian-2- yl)phenyl hex-3- enoate
 
 

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 Cl (E)-4-chloro- 2-(1,3- dithian-2- yl)phenyl hex-3-enoate (Z)-2-chloro- 2-(1,3- dithian-2- yl)phenyl hex-3-enoate
 
 

OG Complex Work Unit Chemistry
 Br (E)-4-bromo- 2-(1,3- dithian-2- yl)phenyl hex-3-enoate (Z)-2-bromo- 2-(1,3- dithian-2- yl)phenyl hex-3-enoate
 
 

OG Complex Work Unit Chemistry
 OCH3 (E)-2-(1,3- dithian-2- yl)-4- methoxy- phenyl hex-3-enoate (Z)-4-(1,3- dithian-2- yl)-4-methoxy- phenyl hex-3-enoate
 
 

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 H 2-(1,3- dithian-2- yl)phenyl 5- methyl- hexanoate 4-(1,3- dithian-2- yl)phenyl 5- methyl- hexanoate
 
 

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 Cl 4-chloro-2- (1,3- dithian-2- yl)phenyl 5-methyl- hexanoate 2-chloro-4-(1,3- dithian-2- yl)phenyl 5-methyl hexanoate
 
 

OG Complex Work Unit Chemistry
 Br 4-bromo-2- (1,3-dithian- 2-yl)phenyl 5-methyl- hexanoate 2-bromo-4- (1,3- dithian-2- yl)phenyl 5-methyl hexanoate
and
 
 
 
 
 

OG Complex Work Unit Chemistry
 OCH3 2-(1,3- dithian-2-yl) 4-methoxy- phenyl 5- methyl- hexanoate 4-(1,3-dithian-2-yl) 2-methoxy- phenyl 5 methyl hexanoate.