US5157053A
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US
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Bicycloalky, tricycloalkyl, azabicycloalkyl, and azatricycloalkyl thio amides used to treat inflammation, allergy, asthma and skin disorders
Assignee: GD Searle LLC
•
Filing: 1990-10-19
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Granted: 1992-10-20
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Expires: 2010-10-19
Abstract
Abstract The compounds of this invention are bicyclic, tricyclic, azabicyclic and azatricyclic amides represented by the formula: ##STR1## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR2## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; x is thio, sulfinyl or sulfonyl; Alk is straight or branched chain lower alkylene; R 3 is selected from the group-consisting of a bicycloalkylamino, tricycloalkylamino, azabicycloalkyl, azatricycloalkyl, aszabicycloalkylamino, azatricycloalkylamino or dicycloalkylamino, The compounds are useful as anti-inflammatory and anti-allergy agents.
Inventors
- 👤 Richard A. Mueller
- 👤 Richard A. Partis
- 👤 James R. Deason
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 15:02
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; C07D453/00; C07D453/02
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
102 words
A method of treating inflammation comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR28## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR29## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 2
Independent Claim
102 words
A method of treating inflammation comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR28## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR29## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 3
Dependent Claim
27 words
A method according to claim 1 wherein said compound is selected from the group consisting of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide; 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,-tricyclo[3.3.1.1.sup.3,7 ]-dec-1-yl propanamide; 3-[[3,5-bis(1,1-dimethylethyl-4-hydroxyphenyl]thio]-N-(6,6-dimethylbicyclo-[3.1.1]hept-2-yl) propanamide; N-endo-bicyclo-[2.2.1]hept-2-yl-3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxypheny]thio]propanamide; and 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.1.sup.3,7 ]dec-2-yl propanamide.
Claim 4
Dependent Claim
19 words
A method according to claim 1 wherein R 1 and R 2 each are 1,1-dimethylethyl and X is thio.
Claim 5
Independent Claim
102 words
A method of treating allergy comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR30## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR31## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 6
Independent Claim
102 words
A method of treating allergy comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR30## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR31## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 7
Dependent Claim
27 words
A method according to claim 4 wherein said compound is selected from the group consisting of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide; 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,-tricyclo[3.3.1.1.sup.3,7 ]-dec-1-yl propanamide; 3-[[3,5-bis(1,1-dimethylethyl-4-hydroxyphenyl]thio]-N-(6,6-dimethylbicyclo-[3.1.1]hept-2-yl) propanamide; N-endo-bicyclo-[2.2.1]hept-2-yl-3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxypheny]thio]propanamide; and 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.1.sup.3,7 ]dec-2-yl propanamide.
Claim 8
Dependent Claim
19 words
A method according to claim 4 wherein R 1 and R 2 each are 1,1-dimethylethyl and X is thio.
Claim 9
Independent Claim
102 words
A method of treating asthma comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR32## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR33## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 10
Independent Claim
102 words
A method of treating asthma comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR32## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR33## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 11
Dependent Claim
27 words
A method according to claim 7 wherein said compound is selected from the group consisting of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide; 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,-tricyclo[3.3.1.1.sup.3,7 ]-dec-1-yl propanamide; 3-[[3,5-bis(1,1-dimethylethyl-4-hydroxyphenyl]thio]-N-(6,6-dimethylbicyclo-[3.1.1]hept-2-yl) propanamide; N-endo-bicyclo-[2.2.1]hept-2-yl-3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxypheny]thio]propanamide; and 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.1.sup.3,7 ]dec-2-yl propanamide.
Claim 12
Dependent Claim
19 words
A method according to claim 7 wherein R 1 and R 2 each are 1,1-dimethylethyl and X is thio.
Claim 13
Independent Claim
104 words
A method of treating proliferative skin disease comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR34## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR35## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 14
Independent Claim
104 words
A method of treating proliferative skin disease comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound of the formula ##STR34## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR35## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 15
Dependent Claim
27 words
A method according to claim 10 wherein said compound is selected from the group consisting of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide; 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,-tricyclo[3.3.1.1.sup.3,7 ]-dec-1-yl propanamide; 3-[[3,5-bis(1,1-dimethylethyl-4-hydroxyphenyl]thio]-N-(6,6-dimethylbicyclo[3.1.1]hept-2-yl) propanamide; N-endo-bicyclo-[2.2.1]hept-2-yl-3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanamide; and 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.1.sup.3,7 ]dec-2-yl propanamide.
Claim 16
Dependent Claim
19 words
A method according to claim 10 wherein R 1 and R 2 each are 1,1-dimethylethyl and X is thio.
Claim 17
Independent Claim
107 words
A method of treating 5-lipoxygenase mediated conditions which comprises administering to a patient in need of such treatment a therapeutically effective 5-lipoxygenase inhibiting amount of a compound of the formula ##STR36## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR37## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 18
Independent Claim
107 words
A method of treating 5-lipoxygenase mediated conditions which comprises administering to a patient in need of such treatment a therapeutically effective 5-lipoxygenase inhibiting amount of a compound of the formula ##STR36## wherein: R 1 and R 2 are the same or different members of the group consisting of halo, phenyl, substituted phenyl and a ##STR37## group wherein n, m and p are independently an integer of from 1 to 8 provided that n+m+p is equal to or less than 10; X is thio or sulfinyl; Alk is straight or branched chain lower alkylene, and R 3 is selected from the group consisting of bicycloalkylamino, tricycloalkylamino, and dicycloalkylamino.
Claim 19
Dependent Claim
15 words
A method according to claim 13 wherein R 1 and R 2 each are ##STR38##
Claim 20
Dependent Claim
15 words
A method according to claim 14 wherein R 1 and R 2 each are 1,1-dimethylethyl.
Claim 21
Dependent Claim
15 words
A method according to claim 13 wherein R 1 and R 2 each are halo.
Claim 22
Dependent Claim
15 words
A method according to claim 13 wherein R 1 and R 2 each are phenyl.
Claim 23
Dependent Claim
10 words
A method according to claim 13 wherein X is thio.
Claim 24
Dependent Claim
10 words
A method according to claim 13 wherein X is sulfinyl.
Claim 25
Dependent Claim
10 words
A method according to claim 15 wherein X is thio.
Claim 26
Dependent Claim
27 words
A method according to claim 13 wherein said compound is selected from the group consisting of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,N-dicyclohexylpropanamide; 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N,-tricyclo[3.3.1.1.sup.3,7 ]-dec-1-yl propanamide; 3-[[3,5-bis(1,1-dimethylethyl-4-hydroxyphenyl]thio]-N-(6,6-dimethylbicyclo-[3.1.1]hept-2-yl) propanamide: N-endo-bicyclo-[2.2.1]hept-2-yl-3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanamide; and 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-N-tricyclo[3.3.1.1.sup.3,7 ]dec-2-yl propanamide.
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