US4833164A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-substituted-1-naphthols, pharmaceutical compositions of, and their use as 5-lipoxygenase inhibitors
Assignee: Bristol Myers Squibb Pharma Co
•
Filing: 1986-03-19
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Granted: 1989-05-23
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Expires: 2006-03-19
Abstract
Abstract 2-Substituted-1-naphthols are 5-lipoxygenase inhibitors which make them useful in the treatment of inflammation, obstructive lung diseases and/or psoriasis. Useful 2-substituent groups are alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkenyls, the groups CH 2 --C.tbd.C--(CH 2 ) m R 5 and CH═CH--(CH 2 ) n R 5 (where m is 1-4, n is 0-3 and R 5 includes phenyl, COOR 9 , where R 9 is H or alkyl of 1-4 carbons, AR 6 (where A is a methylene chain and R 6 is a variety of groups including Cl, Br, I, CHO, CN, COOR 9 , NH 2 , SC(NH)NH 2 , phenyl, P(O)(OR 9 ) 2 , etc.), and CHR 7 R 21 (where R 7 is a variety of aromatic and heterocyclic groups and R 21 is H, optionally substituted phenyl and a variety of heterocyclic groups).
Inventors
- 👤 Douglas G. Batt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 13:18
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; C07C; C07C215/00; C07C215/46; C07C215/48; C07C215/54; C07C255/00; C07C309/00; C07C317/00; C07C323/00; C07C335/00; C07C335/30; C07C335/32; C07C39/00; C07C39/12; C07C39/14; C07C39/205; C07C39/225; C07C39/23; C07C39/24; C07C39/38; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1782; C07C43/20; C07C43/23; C07C43/257; C07C43/295; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07C65/00; C07C65/01; C07C65/105; C07C65/11; C07C65/21; C07C65/24; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/46; C07D213/50; C07D295/04; C07D295/08; C07D295/096; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/46; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4056
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
175 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and a 5-lipoxygenase inhibiting amount of a compound having the formula: ##STR47## wherein R 1 is H; R 2 and R 3 independently are H, CH 3 , C 2 H 5 , OCH 3 , or OC 2 H 5 ; R 4 is ##STR48## R 7 is C 3 -C 8 cycloalkyl ##STR49## R 9 is H or C 1 -C 4 alkyl; R 12 and R 13 independently are H, C 1 -C 4 alkyl, or together are (CH 2 ) 4-5 ; R 14 is H, C 1 -C 4 alkyl, OR 9 , O-phenyl, O-benzyl, CF 3 , Cl, Br, I, N(R 12 ) (R 13 ), or S(O) w R 9 where w is 0-2 with the proviso that is w is 1 then R 9 is not H; and R 15 and R 16 are independently H, C 1 -C 4 alkyl, OR 9 , O-benzyl, F or Cl, and R 21 is H, or a pharmaceutically suitable salt thereof.
Claim 2
Dependent Claim
175 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and a 5-lipoxygenase inhibiting amount of a compound having the formula: ##STR47## wherein R 1 is H; R 2 and R 3 independently are H, CH 3 , C 2 H 5 , OCH 3 , or OC 2 H 5 ; R 4 is ##STR48## R 7 is C 3 -C 8 cycloalkyl ##STR49## R 9 is H or C 1 -C 4 alkyl; R 12 and R 13 independently are H, C 1 -C 4 alkyl, or together are (CH 2 ) 4-5 ; R 14 is H, C 1 -C 4 alkyl, OR 9 , O-phenyl, O-benzyl, CF 3 , Cl, Br, I, N(R 12 ) (R 13 ), or S(O) w R 9 where w is 0-2 with the proviso that is w is 1 then R 9 is not H; and R 15 and R 16 are independently H, C 1 -C 4 alkyl, OR 9 , O-benzyl, F or Cl, and R 21 is H, or a pharmaceutically suitable salt thereof.
Claim 3
Dependent Claim
10 words
The composition of claim 1 wherein R 7 is ##STR50##
Claim 4
Dependent Claim
35 words
The composition of claim 2 wherein R 14 is H, C 1-4 alkyl, OR 9 , Cl, Br, or I; and R 15 and R 16 are independently H, OR 9 , F, or Cl.
Claim 5
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(3-bromophenylmethyl)-1-naphthol.
Claim 6
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(2-fluorophenylmethyl)-1-naphthol.
Claim 7
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(4-fluorophenylmethyl)-1-naphthol.
Claim 8
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(4-methoxyphenylmethyl)-1-naphthol.
Claim 9
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(3-methoxyphenylmethyl)-1-naphthol.
Claim 10
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(4-methylthiophenylmethyl)-1-naphthol.
Claim 11
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(4-(N,N-dimethylamino)phenylmethyl)-1-naphthol.
Claim 12
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(3-trifluoromethylphenylmethyl)-1-naphthol.
Claim 13
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(phenylmethyl)-1-naphthol.
Claim 14
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(3-fluorophenylmethyl)-1-naphthol.
Claim 15
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-[(3,4,5-trimethoxyphenyl)methyl]-1-naphthol.
Claim 16
Dependent Claim
10 words
the composition of claim 1 wherein the compound is 2-[(3,4-dimethoxyphenyl)methyl]-1-naphthol.
Claim 17
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(3-chlorophenylmethyl)-1-naphthol.
Claim 18
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(4-ethoxyphenylmethyl)-1-naphthol.
Claim 19
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 2-(4-bromophenylmethyl)-1-naphthol.
Claim 20
Dependent Claim
10 words
The composition of claim 1 wherein the compound is 5,8-dimethyl-2-(phenylmethyl)-1-naphthol.
Claim 21
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 1.
Claim 22
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 2.
Claim 23
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 3.
Claim 24
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 4.
Claim 25
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 5.
Claim 26
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 6.
Claim 27
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 7.
Claim 28
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 8.
Claim 29
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 9.
Claim 30
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 10.
Claim 31
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 11.
Claim 32
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 12.
Claim 33
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 13.
Claim 34
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 14.
Claim 35
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 15.
Claim 36
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 16.
Claim 37
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 17.
Claim 38
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 18.
Claim 39
Dependent Claim
24 words
A method of inhibiting 5-lipoxygenase in a mammal which comprises administering to the mammal an effective amount of a compound defined in claim 19.
Claim 40
Dependent Claim
159 words
A compound having the formula: ##STR51## wherein R 1 is H, R 2 and R 3 independently are H, CH 3 , C 2 H 5 , CH 3 O, or C 2 H 5 O; R 4 is ##STR52## R 7 is C 3 -C 8 cycloalkyl, ##STR53## R 9 is H or C 1 -C 4 alkyl; R 12 and R 13 independently are H, C 1 -C 4 alkyl, or together are (CH 2 ) 4-5 ; R 14 is C 1 -C 4 alkyl, OR 9 , O-phenyl, O-benzyl, CF 3 , Cl, Br, I, N(R 12 ) (R 13 ), or S(O) w R 9 where w is 0-2 with the proviso that if w is 1 then R 9 is not H; and R 15 and R 16 are independently H, C 1 -C 4 alkyl, OR 9 , O-benzyl, F or Cl; and R 21 is H, subject to the following provisos:
Claim 41
Dependent Claim
159 words
A compound having the formula: ##STR51## wherein R 1 is H, R 2 and R 3 independently are H, CH 3 , C 2 H 5 , CH 3 O, or C 2 H 5 O; R 4 is ##STR52## R 7 is C 3 -C 8 cycloalkyl, ##STR53## R 9 is H or C 1 -C 4 alkyl; R 12 and R 13 independently are H, C 1 -C 4 alkyl, or together are (CH 2 ) 4-5 ; R 14 is C 1 -C 4 alkyl, OR 9 , O-phenyl, O-benzyl, CF 3 , Cl, Br, I, N(R 12 ) (R 13 ), or S(O) w R 9 where w is 0-2 with the proviso that if w is 1 then R 9 is not H; and R 15 and R 16 are independently H, C 1 -C 4 alkyl, OR 9 , O-benzyl, F or Cl; and R 21 is H, subject to the following provisos:
Claim 42
Dependent Claim
41 words
if R 1 , R 2 , and R 3 are all H, then R 4 is not 4-chlorophenylmethyl, or 4-methylphenylmethyl; and 2. if R 2 or R 3 is 6-OCH 3 , then R 4 is not 4-chlorophenylmethyl or 4-methylphenylmethyl.
Claim 43
Dependent Claim
41 words
if R 1 , R 2 , and R 3 are all H, then R 4 is not 4-chlorophenylmethyl, or 4-methylphenylmethyl; and 2. if R 2 or R 3 is 6-OCH 3 , then R 4 is not 4-chlorophenylmethyl or 4-methylphenylmethyl.
Claim 44
Dependent Claim
10 words
A compound of claim 39 wherein R 7 is ##STR54##
Claim 45
Dependent Claim
36 words
A compound of claim 40 wherein R 14 is C 1 -C 4 alkyl, OR 9 , Cl, Br, or I; and R 15 and R 16 are independently H, OR 9 , .F, or Cl.
Claim 46
Dependent Claim
8 words
The compound of claim 39 which is 2-(3-bromophenylmethyl)-1-naphthol.
Claim 47
Dependent Claim
8 words
The compound of claim 39 which is 2-(2-fluorophenylmethyl)-1-naphthol.
Claim 48
Dependent Claim
8 words
The compound of claim 39 which is 2-(4-fluorophenylmethyl)-1-naphthol.
Claim 49
Dependent Claim
8 words
The compound of claim 39 which is 2-(3-fluorophenylmethyl)-1-naphthol.
Claim 50
Dependent Claim
8 words
The compound of claim 39 which is 2-[(3,4,5-trimethoxyphenyl)methyl]-1-naphthol.
Claim 51
Dependent Claim
8 words
The compound of claim 39 which is 2-[(3,4-dimethoxyphenyl)methyl]-1-naphthol.
Claim 52
Dependent Claim
8 words
The compound of claim 39 which is 2-(3-chlorophenylmethyl)-1-naphthol.
Claim 53
Dependent Claim
8 words
The compound of claim 39 which is 2-(4-ethoxyphenylmethyl)-1-naphthol.
Claim 54
Dependent Claim
8 words
The compound of claim 39 which is 2-(4-bromophenylmethyl)-1-naphthol.
Claim 55
Dependent Claim
8 words
The compound of claim 39 which is 5,8-dimethyl-2-(phenylmethyl)-1-naphthol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-05-22 | 1992-11-21 | 1993-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-22 | 1996-11-21 | 1997-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-22 | 2000-11-21 | 2001-05-23 | $7700.00 | Window Closed / Lapsed |