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US4567184A Expired / Lapsed US ⏱️ 0.0 years remaining

Certain aryl or hetero-aryl derivatives of 1-hydroxy-pentane or 1-hydroxy-hexane which are useful for treating inflammation and allergies

Assignee: USV Pharmaceutical Corp
•
Filing: 1983-09-09
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Granted: 1986-01-28
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Expires: 2003-09-09
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Abstract

Abstract Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof, wherein R 1 and R 2 are independently hydrogen, alkyl, carboxy, alkylcarboxy, arylcarboxy, alkyl carbalkoxy, alkanoyl, formyl, nitrile, amino, amino alkyl, alkylamine, carboxamide, halo, trihalomethyl, hydroxy, alkoxy, aryloxy, nitro, sulfonyl, sulfonamide, thio, alkylthio, or R 1 and R 2 can be taken together to form a phenyl ring; B is C or N, in which N can be in any position of the ring; X is O, S, NR 4 , CH 2 Z, CH═N, CH═CH, C.tbd.C, CH 2 ZCH 2 , C═O, C═CR or WC═O; Y is CHCH 2 , C═CH, C--CH 2 , CHCHR 5 , CHC(R 5 ) 2 or CC(R 5 ) 2 ; R 3 is O, OH, OR 4 , SH, SR 4 , NH, HNR 4 or N(R 4 ) 2 ; and M is an integer from 0 to 10; wherein Z is O, S or NR 4 ; R 4 is H, alkyl or aryl; W is O, S or NR 4 ; and R 5 is H, alkyl or fluoro have antiinflammatory and antiallergic activities.

Inventors

  • 👤 John H. Musser
  • 👤 Utpal R. Chakraborty

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 16:07
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07C; C07C229/00; C07C229/38; C07C29/00; C07C29/36; C07C29/38; C07C29/40; C07C309/00; C07C37/00; C07C37/11; C07C37/20; C07C43/00; C07C43/02; C07C43/20; C07C43/23; C07C45/00; C07C45/27; C07C45/30; C07C45/305; C07C45/44; C07C47/00; C07C47/52; C07C47/575; C07C49/00; C07C49/76; C07C49/84; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07C65/00; C07C65/21; C07C65/24; C07D213/60; C07D213/78; C07D213/79; C07D215/00; C07D215/02; C07D215/12; C07D215/14

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 113 words
A compound of the formula: ##STR9## and pharmaceutically acceptable salts thereof, wherein R 1 and R 2 are each independently H, an alkyl group having from 1 to about 6 carbon atoms, and one of the terms R 1 and R 2 may comprise CF 3 ; COOH; COO-lower alkyl or R 1 and R 2 combine with the six-membered ring to which they are attached to form naphthyl; quinoline or isoquinoline; B is C or N; X is CH 2 O Y is CHCH 2 or C(R 5 )CH 2 wherein R 5 is H or lower alkyl; R 3 is OH; M is an integer from about 2 to about 3.
Claim 2
Dependent Claim 113 words
A compound of the formula: ##STR9## and pharmaceutically acceptable salts thereof, wherein R 1 and R 2 are each independently H, an alkyl group having from 1 to about 6 carbon atoms, and one of the terms R 1 and R 2 may comprise CF 3 ; COOH; COO-lower alkyl or R 1 and R 2 combine with the six-membered ring to which they are attached to form naphthyl; quinoline or isoquinoline; B is C or N; X is CH 2 O Y is CHCH 2 or C(R 5 )CH 2 wherein R 5 is H or lower alkyl; R 3 is OH; M is an integer from about 2 to about 3.
Claim 3
Dependent Claim 28 words
A compound of claim 1 of the formula ##STR10## and pharmaceutically acceptable salts thereof, wherein X, Y, R 3 and M are as defined previously in claim 1.
Claim 4
Dependent Claim 32 words
A compound of claim 1 of the formula ##STR11## and pharmaceutically acceptable salts thereof, wherein: B is N; and X, Y, R 3 and M are as previously defined in claim 1.
Claim 5
Dependent Claim 32 words
A compound of claim 1 of the formula ##STR12## and the pharmaceutically acceptable salts thereof, wherein: B is N; and X, R 3 and M are as previously defined in claim 1.
Claim 6
Dependent Claim 4 words
The compound methyl 3-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzoate.
Claim 7
Dependent Claim 4 words
The compound methyl 3-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzoate.
Claim 8
Dependent Claim 4 words
The compound, methyl 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzoate.
Claim 9
Dependent Claim 4 words
The compound, methyl 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]benzoate.
Claim 10
Dependent Claim 3 words
The compound, 1-(3-benzyloxyphenyl)-1-methyl-1-pentanol.
Claim 11
Dependent Claim 3 words
The compound, 1-(3-benzyloxyphenyl)-1-methyl-1-pentanol.
Claim 12
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]pyridine and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]pyridine and the pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim 4 words
The compound, 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]pyridine hydrochloride.
Claim 15
Dependent Claim 4 words
The compound, 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]pyridine hydrochloride.
Claim 16
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxhexyl)phenoxy]methyl]quinoline and the pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxhexyl)phenoxy]methyl]quinoline and the pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim 4 words
The compound, 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]quinoline hydrochloride.
Claim 19
Dependent Claim 4 words
The compound, 2-[[3-(1-hydroxyhexyl)phenoxy]methyl]quinoline hydrochloride.
Claim 20
Dependent Claim 10 words
The compound, 2-(3-(2-hydroxyheptyl)phenoxy)methyl quinoline and the pharmaceutically acceptable salts thereof.
Claim 21
Dependent Claim 10 words
The compound, 2-(3-(2-hydroxyheptyl)phenoxy)methyl quinoline and the pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim 5 words
The compound, 2-(3-(2-hydroxyheptyl)phenoxy)methyl quinoline hydrochloride.
Claim 23
Dependent Claim 5 words
The compound, 2-(3-(2-hydroxyheptyl)phenoxy)methyl quinoline hydrochloride.
Claim 24
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxy-1-methylhexyl)phenoxy]methyl]quinoline and the pharmaceutically acceptable salts thereof.
Claim 25
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxy-1-methylhexyl)phenoxy]methyl]quinoline and the pharmaceutically acceptable salts thereof.
Claim 26
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxy-1-methylhexyl)phenoxy]methyl]pyridine and the pharmaceutically acceptable salts thereof.
Claim 27
Dependent Claim 9 words
The compound, 2-[[3-(1-hydroxy-1-methylhexyl)phenoxy]methyl]pyridine and the pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim 25 words
A method of treating inflammatory and allergic conditions in a mammal by administering to said mammal an effective amount of a compound of claim 1.

References Cited (Backward Citations)

US4200763A Cited
US4202833A Cited
JPS55124777A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-01-27 1989-07-29 1990-01-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-01-27 1993-07-29 1994-01-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-01-27 1997-07-29 1998-01-28 $7700.00 Window Closed / Lapsed

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