EP0200101A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Aryl and heteroaryl ethers as agents for the treatment of hypersensitive aliments
Assignee: USV Pharmaceutical Corp
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Filing: 1986-04-16
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Granted: —
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Expires: 2006-04-16
Abstract
Abstract The present invention is concerned with the therapeutic composition comprising as an active ingredient a compound of the formula: and salts thereof; wherein Ar and Ar, are independently phenyl, naphthyl or a nitrogen, oxygen, or sulfur heterocyclic ring; R,, 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, tetrahydropyranylmethyl, tetrazole, tetrazole lower alkyl, formyl amino or lower alkanoylamino; R, is 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, tetrahydropyranylmethyl, or tetrazole, or tetrazole lower alkyl or R s ; R s is lower alkoxy, phenyl, OH, CO 2 R 6 cyclic or heterocyclic structures.
Inventors
- 👤 Raymond Youssefyeh
- 👤 Utpal Chakraborty
- 👤 Ernest Magnien
- 👤 Rohit Desai
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 05:24
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: 18
Claim 1
Independent Claim
14 words
A therapeutic composition comprising as an ac- itve ingredient a compound of the formula:
Claim 2
Dependent Claim
14 words
A therapeutic composition comprising as an ac- itve ingredient a compound of the formula:
Claim 3
Dependent Claim
259 words
and salts thereof; wherein Ar and Ar, are independently phenyl, naphthyl or a nitrogen, oxygen, or sulfur heterocyclic ring; 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, tetrahydropyranylemthl, tetrazole, tetrazole lower alkyl, formylamino, or loweralkanoylamino; R 4 is 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, tetrahydropyranylmethyl, tetrazole, tetrazole lowe alkyl or R s ; R s is lwoer alkoxy, phenyl, OH, CO 2 R 6 , R 6 is H, lower alkyl, aryl, or lower aralkyl; R 7 is H, lower alkyl, , or 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,, 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., CH=CH, CH 2 -CH=CH, COO-, or CH 2 ; with the proviso that when Y is O, S, or NR., R, is not OH or CO 2 R 6 .
Claim 4
Dependent Claim
259 words
and salts thereof; wherein Ar and Ar, are independently phenyl, naphthyl or a nitrogen, oxygen, or sulfur heterocyclic ring; 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, tetrahydropyranylemthl, tetrazole, tetrazole lower alkyl, formylamino, or loweralkanoylamino; R 4 is 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, tetrahydropyranylmethyl, tetrazole, tetrazole lowe alkyl or R s ; R s is lwoer alkoxy, phenyl, OH, CO 2 R 6 , R 6 is H, lower alkyl, aryl, or lower aralkyl; R 7 is H, lower alkyl, , or 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,, 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., CH=CH, CH 2 -CH=CH, COO-, or CH 2 ; with the proviso that when Y is O, S, or NR., R, is not OH or CO 2 R 6 .
Claim 5
Dependent Claim
10 words
The therapeutic composition of Claim 1 wherein Ar, is phenyl.
Claim 6
Dependent Claim
259 words
The therapeutic composition of Claims 1-2 wherein the compound has the formula: and salts thereof wherein Ar is phenyl, naphthyl, quinolyl or isoquinolyl; R, and R 2 are each independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, carboxy, formyl, phenyl, phenoxy, benzyloxy, loweralkylamino, di-loweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, formyl amino or lower alkanoyl amino; 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 NF 8 ; Y is a chemical bond or 0; R 4 is lower alkoxy, phenyl, OH, CO 2 R 6 , R 6 is H, lower alkyl, aryl or lower aralkyl; R 7 is H, lower alkyl, or , or R 8 is H or lower alkyl; each M is independently 0, S, or NR 8 ; m is 0 to 5; n is 0 or 1; X is O, S, NR 8 ; Z, Z,, 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, 0, S, NR, CO, CHOR 8 , CH=CH, CH 2 -CH=CH, COO-, or CH 2 ; with the proviso that when Y is O, S, or NR,, R 4 is not OH or CO 2 R 6 .
Claim 7
Dependent Claim
20 words
The therapeutic composition of Claims 1-3 wherein M is O, Z is CH 2 and Z, is a chemical bond.
Claim 8
Dependent Claim
99 words
The therapeutic composition of Claims 1-4 wherein the compound has the formula: and salts thereof, wherein R, is H, lower alkyl, hydroxy, lower alkoxy, halo, CF 3 , carboxy, carbalkoxy, formyl amino or loweral- koanoylamino; R 6 is H or lower alkyl; 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 and R 4 is lower alkoxy, lower alkyl, R 7 is H, lower alkyl, or ,and n is 0 or 1,
Claim 9
Dependent Claim
10 words
The therapeutic composition of Claims 1-5 wherein R 4 is
Claim 10
Dependent Claim
45 words
A therapeutic composition according to Claim 1 wherein the compound is 2-phenoxymethyl quinoline; 2-(p-nitrophenoxymethyl)quinoline; 2-(p-methoxyphenoxymethyl)quinoline; 2-phenoxymethylisoquinoline; 2-(3-(carboethoxyphenoxy)methyl)quinoline; 2-(3-(carboxyphenoxy)methyl)quinoline; 2-(3-cyanophenoxy)methyl)quinoline; 2-(3-(trifluoromethylphenoxy)methyl)quinoline; 2-(3-(fluorophenoxy)methyl)quinoline; 2-(3-(chlorophenoxy)methyl)quinoline; 2-(3-butoxyphenoxy)methyl)quinoline; 2-(m-tolyloxymethyl)quinoline; 2-(3-(benzyloxy)methyl)quinoline; 2-(4-(phenoxyphenoxy)methly)quinoline; 2-(3,5-dichlorophenoxymethyl)quinoline; 2-(3,4-dimethylphenoxymethyl)quinoline; 2-(4-ftuorophenoxymethyl)-6-methoxyquinoline; 2-(3-butoxyphenoxymethyl)-6-methoxyquinoline; 2-(4-fluorophenoxymethyl)-8-methoxyquinoline; 2-(3-carboxyphenoxymethyl)-8-methoxyquinoline; 2-(3-carboxyphenoxymethyl)-6-methoxyquinoline; 2-(3-trifluoromethylphenoxymethyl)-7-methoxyquinoline; 2-(3-chlorophenoxymethyl)-6-methoxyquinoline; 8-(3-n-butoxy)benzyloxyquinoline; 1-(3-n-butoxyphenoxymethyl)isoquinoline; 2-(3-trifluorophenoxy)-6-methoxyquinoline; 2-(3-carboxyphenoxy)-7-methoxyquinoline; 8-(3-n-butylbenzyloxy)quinoline; or 1-(3-carboxyphenoxymethyl)isoquinoline; or salts thereof.
Claim 11
Dependent Claim
245 words
Compound of the formula: and salts thereof, wherein Ar is phenyl, naphthyl, quinoline or isoquinoline; R, and R 2 are each independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, carboxy, formyl, phenyl, phenoxy, benzyloxy, loweralkylamino, di-loweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, or Z, Z,, 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 0, S, or NR 8 ; Y is a chemical bond or O; R4 is lower alkoxy, phenyl, OH, CO 2 R 6 , R 6 is H, lower alkyl, aryl, or lower aralkyl; R 7 is H, lower alkyl, , or 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 Z3 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, 0, S, NR, CO, GHOR 8 , CH=CH, CH 2 -CH=CH, COO-, or CH 2 ; with the proviso that when Y is O, S, or NR 8 , R 4 is not OH or CO 2 R 6 .
Claim 12
Dependent Claim
245 words
Compound of the formula: and salts thereof, wherein Ar is phenyl, naphthyl, quinoline or isoquinoline; R, and R 2 are each independently H, lower alkyl, lower alkoxy, hydroxy, halo, trihalomethyl, hydroxy-lower alkyl, carboxy, formyl, phenyl, phenoxy, benzyloxy, loweralkylamino, di-loweralkylamino, cyano, lower alkanoyloxy, carbamoyl, lower alkoxy-lower alkoxy, lower carbalkoxy-lower alkoxy, or Z, Z,, 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 0, S, or NR 8 ; Y is a chemical bond or O; R4 is lower alkoxy, phenyl, OH, CO 2 R 6 , R 6 is H, lower alkyl, aryl, or lower aralkyl; R 7 is H, lower alkyl, , or 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 Z3 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, 0, S, NR, CO, GHOR 8 , CH=CH, CH 2 -CH=CH, COO-, or CH 2 ; with the proviso that when Y is O, S, or NR 8 , R 4 is not OH or CO 2 R 6 .
Claim 13
Dependent Claim
20 words
The compound according to Claim 8 wherein M is 0, Z is CH 2 and Z, is a chemical bond.
Claim 14
Dependent Claim
100 words
The compound according to Claims 8-9 wherein the compound has the formula: . and salts thereof, wherein R, is H, lower alkyl, hydroxy, lower alkoxy, halo, CF 3 , carboxy, carbalkoxy, formylamino or loweralkanoylamino; R 6 is H or lower alkyl; 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 and R 4 is lower alkoxy, lower alkyl, R, is H, lower alkyl, or ,and'n is 0 or 1.
Claim 15
Dependent Claim
10 words
The compound according to Claims 8-10 wherein R 4 is
Claim 16
Dependent Claim
40 words
The compound according to Claim 8 which is 2-(4-(4-Tetrahydropyranomethyl)phenoxymethyl)-quinoline; 2-(4-(Phenoxymethyl)phenoxymethyl)quinoline; 2-[3-(p-Methoxyphenoxymethyl)phenoxymethyl)-quinoline; 2-(3-(2-Methoxyethoxymethyl)phenoxymethyl)-quinoline; 2-(3-(4-Methylpiperazinylmethyl)phenoxymethyl)-quinoline; 5[3-(2-Quinolylmethyloxy)phenyl]tetrazole; 3-[5-3-(2-quinolylmethoxy)phenyltetrazolo]acetate 2-[3-(2-Tetrahydrofuranooxymethyl)-phenoxymethyl]quinoline; 5[3-(2-Quinolylmethoxy)-3-phenoxypropyl]tetrazole; 2-(4-(Morpholinomethyl)phenyloxymethylquinoline; 4-(4'Benzyloxybenzylidine)tetrahydropyran; 5[3-[3-(1-Hydroxyhexyl)phenoxymethyl]phenyl]2-carboxymethyl-2H-tetrazole; 5-[3-[3-(1-Hydroxyhexyl)phenoxymethyl]phenyl]2- carbethoxymethyl-2H-tetrazole; 5-[3-[3-(1-Hydroxyhexyl)phenoxymethyl]phenyl]2H-tetrazole; 3-[5-3-(2-Quinolylmethoxy)phenyltetrazolo]acetic acid; 2-[3-(4-Hydroxy-4-phenylpiperidinomethyl)-phenoxymethyl]quinoline; 1-(3-Benzyloxyphenyl)-1-(4-methoxyphenyl)-methanol; 1-(4-Tetrahydropyrano)-1-[4-(2-quinolinylmethoxy)-benzene]methanol; 1-(4-Methoxyphenyl)-1-[3-(2-quinolinylmethoxy)-benzene]methanol; 3-(2-Quinolylmethytoxy)-3-phenoxybutyronitirile; 5[4-(2-Quinolylmethyloxy)3-phenoxypropyl]-tetrazole; 5[2-(2-Quinolylmethyloxy)3-phenoxypropyl]-tetrazole; 5[3-)2-Quinolylmethyloxy)-4-phenoxybutyl]tetrazole; 5[4-(2-Quinolylmethyloxy)benzyl]tetrazole; 2-(p-Nitrophenoxymethyl)quinoline; or 2-(p-Methoxyphenoxymethyl)quinoline; or salts thereof.
Claim 17
Dependent Claim
74 words
A process for the preparation of a compound according to claims 1-7 as an active ingredient of a therapeutic composition which comprises: (a) reacting a compound of Formula II with a compound of Formula III; or (b) reduction of the coressponding imine of For- mulal; or optionally removing the protecting group when present; or optionally introducing substituents into the compounds by substitution or conversion reactions; or optionally forming pharmaceutically acceptable salts of said compound.
Claim 18
Dependent Claim
69 words
The process for forming a compound according to claims 8-12 which comprises: (a) reacting a compound of Formula IIA as herein defined with a compound of Formula IIIA as herein defined; or (b) reducing the corresponding imine of Formula lA and optionally removing the protecting group when present; and optionally introducing substituents into the compounds by substitution or conversion reactions; and optionally forming pharmaceutically acceptable salts of said compounds.
References Cited (Backward Citations)
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