US4666928A
Expired / Lapsed
US
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Propylphenoxy pyridine carboxylates as leukotriene antagonists
Assignee: Merck Frosst Canada and Co
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Filing: 1984-08-30
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Granted: 1987-05-19
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Expires: 2004-08-30
Abstract
Abstract Compounds having the formula: <IMAGE> I are antagonists of leukotrines of C4, D4 and E4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
Inventors
- 👤 Robert N. Young
- 👤 Joshua Rokach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:39
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; A; A61; A61P; A61P29/00; A61P43/00; C07D213/71; C07D213/78; C07D213/79; C07D213/80
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
366 words
A Compound having the formula: ##STR38## wherein: each Y is independently selected from CR or N, but at least one Y but not both must be N; each n is independently 0 to 6: each R independently represents H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, alkenyl of 2 to 6 carbon atoms which is straight chain or branched, trifluoromethyl, alkoxy of 1 to 6 carbon atoms which is straight chain or branched, SH, thioalkyl of 1 to 6 carbon atoms which is straight chain or branched, halogen, OH, amino, N(R 4 ) 2 , COOR 4 , CH 2 OR 4 , formyl, CN, trifluoromethylthio, or nitro (with the proviso that both R groups are not simultaneously OH, amino, N(R 4 ) 2 , COOR 4 , CH 2 OR 4 , formyl, CN, trifluoromethylthio, or nitro); R' is H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, alkenyl of 2 to 6 carbon atoms which is straight chain or branched, trifluoromethyl, alkoxy of 1 to 6 carbon atoms which is straight chain or branched, thioalkyl of 1 to 6 carbon atoms which is straight chain or branched, halogen, or trifluoromethylthio; R 1 is H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, or alkoxy of 1 to 6 carbon atoms which is straight chain or branched; R 2 is H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, R 4 CO, or R 4 OCH 2 ; R 3 is alkyl of 1 to 6 carbon atoms which is straight chain or branched, alkenyl of 3 to 6 carbon atoms which is straight chain or branched, phenyl, or phenyl substituted by one or more R; R 4 is independently H or alkyl of 1 to 6 carbon atoms which is straight chain or branched; R 5 is independently H, OH, alkyl of 1 to 4 carbons, or both R 5 's are combined to create a doubly bonded oxygen (═O); X 1 and X 2 are each independently oxygen, sulfur, sulfoxide, or sulfone; and a pharmaceutically acceptable salt or acid addition salt thereof.
Claim 2
Dependent Claim
366 words
A Compound having the formula: ##STR38## wherein: each Y is independently selected from CR or N, but at least one Y but not both must be N; each n is independently 0 to 6: each R independently represents H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, alkenyl of 2 to 6 carbon atoms which is straight chain or branched, trifluoromethyl, alkoxy of 1 to 6 carbon atoms which is straight chain or branched, SH, thioalkyl of 1 to 6 carbon atoms which is straight chain or branched, halogen, OH, amino, N(R 4 ) 2 , COOR 4 , CH 2 OR 4 , formyl, CN, trifluoromethylthio, or nitro (with the proviso that both R groups are not simultaneously OH, amino, N(R 4 ) 2 , COOR 4 , CH 2 OR 4 , formyl, CN, trifluoromethylthio, or nitro); R' is H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, alkenyl of 2 to 6 carbon atoms which is straight chain or branched, trifluoromethyl, alkoxy of 1 to 6 carbon atoms which is straight chain or branched, thioalkyl of 1 to 6 carbon atoms which is straight chain or branched, halogen, or trifluoromethylthio; R 1 is H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, or alkoxy of 1 to 6 carbon atoms which is straight chain or branched; R 2 is H, alkyl of 1 to 6 carbon atoms which is straight chain or branched, R 4 CO, or R 4 OCH 2 ; R 3 is alkyl of 1 to 6 carbon atoms which is straight chain or branched, alkenyl of 3 to 6 carbon atoms which is straight chain or branched, phenyl, or phenyl substituted by one or more R; R 4 is independently H or alkyl of 1 to 6 carbon atoms which is straight chain or branched; R 5 is independently H, OH, alkyl of 1 to 4 carbons, or both R 5 's are combined to create a doubly bonded oxygen (═O); X 1 and X 2 are each independently oxygen, sulfur, sulfoxide, or sulfone; and a pharmaceutically acceptable salt or acid addition salt thereof.
Claim 3
Dependent Claim
35 words
A Compound according to claim 1 wherein: X 1 is O; X 2 is O, S, SO, or SO 2 ; one Y is N and the other is CH; and each n is 1.
Claim 4
Dependent Claim
30 words
A Compound according to claim 1 said compounds having the formula: ##STR39## wherein each R 1 is alkyl of 1 to 6 carbon atoms which is straight chain or branched.
Claim 5
Dependent Claim
23 words
A compound of claim 1 wherein one Y is N and the other is CH, and X 2 is sulfur, sulfoxide, or sulfone.
Claim 6
Dependent Claim
15 words
A compound of claim 1 wherein X 1 is O and X 2 is S.
Claim 7
Dependent Claim
17 words
A compound of claim 1 wherein X 1 is O and X 2 is SO 2 .
Claim 8
Dependent Claim
12 words
A compound of claim 1: 2-(3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propylthio)-5-carboxypyridine; Methyl 2-(3-(4-acetyl-3-hydroxy-2-propylphenoxypropylthio)pyridine-5-carboxylate; Methyl 2-(3-(4-acetyl-3-hydroxy-2-propylphenoxypropylsulfonyl)pyridine-5-carboxylate; and 2-(3-(4-Acetyl-3-hydroxy-2-propylphenoxy)propylsulfonyl)-5-carboxypyridine.
Claim 9
Dependent Claim
29 words
A pharmaceutical composition, useful in antagonizing leukotriene action in mammals, comprising an amount of a compound of claim 1 effective as a leukotriene antagonist and a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
24 words
A method of antagonizing leukotriene action in a mammal which comprises administering to said mammal an effective amount of a compound of claim 1.
References Cited (Backward Citations)
US4219477A
Cited
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