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US4839369A Expired / Lapsed US ⏱️ 0.0 years remaining

Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments

Assignee: Aventis Pharmaceuticals Inc
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Filing: 1986-03-13
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Granted: 1989-06-13
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Expires: 2006-03-13
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Abstract

Abstract Aryl and Heteroaryl Ethers are used for their anti-inflammatory and anti-allergic properties.

Inventors

  • 👤 Raymond Youssefyeh
  • 👤 Utpal Chakraborty
  • 👤 Ernest Magnien
  • 👤 Rohit Desai

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 06:33
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/23; C07D215/00; C07D215/02; C07D215/12; C07D215/14; C07D309/00; C07D309/16; C07D309/20; C07D309/22; C07D401/00; C07D401/02; C07D401/12; C07D405/00; C07D405/02; C07D405/12

Claims Analysis

Total Claims: 25
Claim 1
Independent Claim 197 words
A therapeutic composition comprising an effective anti-hypersensitive amount of a compound of the formula (R.sub.1)(R.sub.2)Ar--Z--M--Z.sub.1 --Ar.sub.1 (R.sub.3)(Z.sub.2 --Y--Z.sub.3 --R.sub.4) wherein Ar is quinoline or isoquinoline; Ar 1 is phenyl; R 1 , R 2 , and R 3 are independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, alkyl carboxy, carboxy, formyl, lower alkyl carbonyl, aryl, aryloxy, benzyloxy, lower alkylamino, diloweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, nitro, amino, tetrahydro-pyranylmethyl, or tetrazole, or tetrazole lower alkyl; R 4 is ##STR40## R 7 is H, lower alkyl, ##STR41## R 8 is H or lower alkyl; each M is independently O, S, or NR 8 ; m is 0 to 5; n is 0 or 1; X is O, S, NR 8 ; Z, Z 1 , Z 2 , and Z 3 are independently a chemical bond or an alkylene chain containing up to 5 carbon atoms in the principal chain and up to a total of 8 carbon atoms; Y is a chemical bond, O, S, NR, CO, CHOR 8 , CH═CH, CH 2 --CH═CH, COO--, or CH 2 ; or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim 197 words
A therapeutic composition comprising an effective anti-hypersensitive amount of a compound of the formula (R.sub.1)(R.sub.2)Ar--Z--M--Z.sub.1 --Ar.sub.1 (R.sub.3)(Z.sub.2 --Y--Z.sub.3 --R.sub.4) wherein Ar is quinoline or isoquinoline; Ar 1 is phenyl; R 1 , R 2 , and R 3 are independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, alkyl carboxy, carboxy, formyl, lower alkyl carbonyl, aryl, aryloxy, benzyloxy, lower alkylamino, diloweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, nitro, amino, tetrahydro-pyranylmethyl, or tetrazole, or tetrazole lower alkyl; R 4 is ##STR40## R 7 is H, lower alkyl, ##STR41## R 8 is H or lower alkyl; each M is independently O, S, or NR 8 ; m is 0 to 5; n is 0 or 1; X is O, S, NR 8 ; Z, Z 1 , Z 2 , and Z 3 are independently a chemical bond or an alkylene chain containing up to 5 carbon atoms in the principal chain and up to a total of 8 carbon atoms; Y is a chemical bond, O, S, NR, CO, CHOR 8 , CH═CH, CH 2 --CH═CH, COO--, or CH 2 ; or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim 29 words
A method for the treatment of inflammatory or allergic conditions in mammals comprising the administration thereto, in effective anti-inflammatory or anti-allergic doses, of a composition according to claim 1.
Claim 4
Independent Claim 109 words
A method for the treatment of inflammatory or allergic conditions in mammals comprising the administration thereto of an effective therapeutic amount of a compound of the formula ##STR42## wherein: R 1 is hydrogen, alkyl having one to about 5 carbon atoms, halo, triflouromethyl, hydroxy, lower alkoxy, ##STR43## Z 2 and Z 3 are independently a chemical bond or --(CH 2 ) m --; Y is a chemical bond, oxy, carbonyl, carboxyl, hydroxymethylene or loweralkoxymethylene; R 7 is hydrogen, lower alkyl or (CH 2 ) m CO 2 R 8 ; R 8 is hydrogen or lower alkyl; and m is 0-5; or a pharmaceutically acceptable acid addition salt thereof.
Claim 5
Independent Claim 109 words
A method for the treatment of inflammatory or allergic conditions in mammals comprising the administration thereto of an effective therapeutic amount of a compound of the formula ##STR42## wherein: R 1 is hydrogen, alkyl having one to about 5 carbon atoms, halo, triflouromethyl, hydroxy, lower alkoxy, ##STR43## Z 2 and Z 3 are independently a chemical bond or --(CH 2 ) m --; Y is a chemical bond, oxy, carbonyl, carboxyl, hydroxymethylene or loweralkoxymethylene; R 7 is hydrogen, lower alkyl or (CH 2 ) m CO 2 R 8 ; R 8 is hydrogen or lower alkyl; and m is 0-5; or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim 87 words
A compound of the formula ##STR44## wherein: R 1 is hydrogen, alkyl having one to about 5 carbon atoms, halo, triflouromethyl, hydroxy, lower alkoxy, ##STR45## Z 2 and Z 3 are independently a chemical bond or --(CH 2 ) m --; Y is a chemical bond, oxy, carbonyl, carboxyl, hydroxymethylene or loweralkoxymethylene; R 7 is hydrogen, lower alkyl or (CH 2 ) m CO 2 R 8 ; R 8 is hydrogen or lower alkyl; and m is 0-5; or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim 87 words
A compound of the formula ##STR44## wherein: R 1 is hydrogen, alkyl having one to about 5 carbon atoms, halo, triflouromethyl, hydroxy, lower alkoxy, ##STR45## Z 2 and Z 3 are independently a chemical bond or --(CH 2 ) m --; Y is a chemical bond, oxy, carbonyl, carboxyl, hydroxymethylene or loweralkoxymethylene; R 7 is hydrogen, lower alkyl or (CH 2 ) m CO 2 R 8 ; R 8 is hydrogen or lower alkyl; and m is 0-5; or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim 32 words
A pharmaceutical composition for use in treating inflammatory or allergic conditions comprising in admixture with a pharmaceutically acceptable carrier an effective anti-inflammatory or anti-allergic amount of a compound according to claim 4.
Claim 9
Dependent Claim 17 words
A compound according to claim 4 wherein Z 2 is a chemical bond and Y is oxy.
Claim 10
Dependent Claim 19 words
A compound according to claim 4 wherein Z 2 is a chemical bond and Y is a chemical bond.
Claim 11
Dependent Claim 203 words
A compound of the formula ##STR46## Ar is quinoline or isoquinoline; R 1 and R 2 are each independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, carboxy, formly, phenyl, phenoxy, benzyloxy, loweralkylamino, di-loweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, or ##STR47## Z, Z 1 , Z 2 and Z 3 are independently a chemical bond or an alkylene chain containing up to 5 carbon atoms in the principal chain and up to a total of 8 carbon atoms; M is O, S, or NR 8 ; R 5 is ##STR48## R 7 is H, lower alkyl, ##STR49## R 8 is H or lower alkyl; each M is independently O, S, or NR 8 ; m is 0 to 5; n is 0 to 1; X is O, S, NR 8 ; Z, Z 1 , Z 2 , and Z 3 are independently a chemical bond or an alkylene chain containing up to 5 carbon atoms in the principal chain and up to a total of 8 carbon atoms; Y is a chemical bond, O, S, NR, CO, CHOR 8 , CH═CH, CH 2 --CH═CH, COO--, or CH 2 ; or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim 203 words
A compound of the formula ##STR46## Ar is quinoline or isoquinoline; R 1 and R 2 are each independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, carboxy, formly, phenyl, phenoxy, benzyloxy, loweralkylamino, di-loweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, or ##STR47## Z, Z 1 , Z 2 and Z 3 are independently a chemical bond or an alkylene chain containing up to 5 carbon atoms in the principal chain and up to a total of 8 carbon atoms; M is O, S, or NR 8 ; R 5 is ##STR48## R 7 is H, lower alkyl, ##STR49## R 8 is H or lower alkyl; each M is independently O, S, or NR 8 ; m is 0 to 5; n is 0 to 1; X is O, S, NR 8 ; Z, Z 1 , Z 2 , and Z 3 are independently a chemical bond or an alkylene chain containing up to 5 carbon atoms in the principal chain and up to a total of 8 carbon atoms; Y is a chemical bond, O, S, NR, CO, CHOR 8 , CH═CH, CH 2 --CH═CH, COO--, or CH 2 ; or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim 9 words
A compound according to claim 8 which is 2-carboxymethyl-5-[3-(2-quinolylmethyloxy)phenyl]tetrazole.
Claim 14
Dependent Claim 9 words
A compound according to claim 8 which is 5-[3-(4-[2-quinolylmethyloxy]phenoxy)propyl]tetrazole.
Claim 15
Dependent Claim 9 words
A compound according to claim 8 which is 5-[3-(2-[2-quinolylmethyloxy]phenoxy)propyl]tetrazole.
Claim 16
Dependent Claim 9 words
A compound according to claim 8 which is 5-[4-(3-[2-quinolylmethyloxy]phenoxy)butyl]tetrazole.
Claim 17
Dependent Claim 9 words
A compound according to claim 8 which is 5-[4-(2-quinolylmethyloxy)benzyl]tetrazole.
Claim 18
Dependent Claim 88 words
A compound of the formula ##STR50## wherein R 1 is H, C 1-5 alkyl, OR 8 , halo, CF 3 , ##STR51## R 8 is H or lower alkyl; Z 2 is a chemical bond or (CH 2 ) m ; Z 3 is a chemical bond or (CH 2 ) m ; m is 0-5; Y is a chemical bond or ##STR52## and R 5 is ##STR53## R 7 is H, lower alkyl,, or ##STR54## and n is 0 or 1; or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim 88 words
A compound of the formula ##STR50## wherein R 1 is H, C 1-5 alkyl, OR 8 , halo, CF 3 , ##STR51## R 8 is H or lower alkyl; Z 2 is a chemical bond or (CH 2 ) m ; Z 3 is a chemical bond or (CH 2 ) m ; m is 0-5; Y is a chemical bond or ##STR52## and R 5 is ##STR53## R 7 is H, lower alkyl,, or ##STR54## and n is 0 or 1; or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim 7 words
5-[3-(2-Quinolylmethoxy)phenyl]tetrazole or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim 7 words
5-[3-(2-Quinolylmethoxy)phenyl]tetrazole or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim 7 words
2-Carbethoxymethyl-5-[3-(2-quinolylmethyloxy)phenyl]tetrazole or a pharmaceutically acceptable salt thereof.
Claim 23
Dependent Claim 7 words
2-Carbethoxymethyl-5-[3-(2-quinolylmethyloxy)phenyl]tetrazole or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim 7 words
5-[3-(3-[2-Quinolylmethyloxy]phenoxy)propyl]tetrazole or a pharmaceutically acceptable salt thereof.
Claim 25
Dependent Claim 7 words
5-[3-(3-[2-Quinolylmethyloxy]phenoxy)propyl]tetrazole or a pharmaceutically acceptable salt thereof.

References Cited (Backward Citations)

DE189142C Cited
DE181568C Cited
NL110405C Cited
US4244956A Cited
US4567184A Cited
US4661499A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-06-12 1992-12-12 1993-06-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-06-12 1996-12-12 1997-06-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-06-12 2000-12-12 2001-06-13 $7700.00 Window Closed / Lapsed

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