US4939169A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,4-naphthalenediol and 1,4-hydroquinone derivatives
Assignee: Pharmacia and Upjohn Co
•
Filing: 1989-03-13
•
Granted: 1990-07-03
•
Expires: 2009-03-13
Abstract
Abstract Novel 1,4-naphthalenediol and 1,4-hydroquinone derivatives of formula I, II, III and IV and their therapeutic uses as 5-lipoxygenase inhibitors, leukotriene inhibitors, antiinflammatory and/or inhibitors of mucus secretion agents are described. Also provided are novel intermediates useful for the preparation of said derivatives. ##STR1##
Inventors
- 👤 Gordon L. Bundy
- 👤 Chiu-Hong Lin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 18:14
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07C; C07C43/00; C07C43/02; C07C43/20; C07C43/215; C07C43/23; C07C46/00; C07C46/02; C07C46/06; C07C50/00; C07C50/02; C07C50/06; C07C50/10; C07C50/14; C07C50/24; C07C50/26; C07C50/28; C07C50/32; C07C50/38
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
82 words
A compound having the formula wherein R 1 is tetrahydro-2H-pyranyl, --C(O)CH 3 , the residue of an amino acid having the structure --C(O)--CH-(isopropyl)-NH 2 , the N-t-butylcarbonyloxy derivative or the HCl salt thereof, or the HCl salt thereof, or --C(O)--(CH 2 ) 2 --COOH or a pharmaceutically acceptable salt thereof; R 2 is --C.tbd.C--(CH 2 ) m --C.tbd.C--(CH 2 ) p --OR 1 and n is 3 or 4, m is 1 to 5, inclusive and p is 0 to 3 inclusive.
Claim 2
Dependent Claim
82 words
A compound having the formula wherein R 1 is tetrahydro-2H-pyranyl, --C(O)CH 3 , the residue of an amino acid having the structure --C(O)--CH-(isopropyl)-NH 2 , the N-t-butylcarbonyloxy derivative or the HCl salt thereof, or the HCl salt thereof, or --C(O)--(CH 2 ) 2 --COOH or a pharmaceutically acceptable salt thereof; R 2 is --C.tbd.C--(CH 2 ) m --C.tbd.C--(CH 2 ) p --OR 1 and n is 3 or 4, m is 1 to 5, inclusive and p is 0 to 3 inclusive.
Claim 3
Dependent Claim
9 words
A compound of claim 1, 2-(11-hydroxyundeca-4,9-diynyl)-1-hydroxy-4-methoxynaphthalene, bis-(N-t-butylcarbonyloxy valine ester).
Claim 4
Dependent Claim
8 words
A compound of claim 1, 2-(11-hydroxyundeca-4,9-diynyl)-1-hydroxy-4-methoxynaphthalene, bis-(valine ester).
Claim 5
Dependent Claim
9 words
A compound of claim 1, 2-(11-hydroxyundeca-4,9-diynyl)-1-hydroxy-4-methoxynaphthalene, bis(valine ester, hydrochloride).
Claim 6
Dependent Claim
8 words
A compound of claim 1, 2-(11-hydroxyundeca-4,9-diynyl)-1-hydroxy-4-methoxynaphthalene, bis (succinate).
Claim 7
Dependent Claim
9 words
A compound of claim 1, 2-(11-hydroxyundeca-4,9-diynyl)-1-hydroxy-4-methoxynaphthalene, bis(succinate, potassium salt).
Claim 8
Dependent Claim
9 words
A compound of claim 1, 2-(11-hydroxyundeca-4,9-diynyl)-1-hydroxy-4-methoxynaphthalene, bis(succinate, tris-(hydroxymethyl)aminomethyl salt).
Claim 9
Dependent Claim
14 words
A compound of claim 1 selected from the group consisting of 2-(12-tetrahdyropyran-2-yloxydodeca-5,10-diynyl)-1-tetrahydropyran-2-yloxy)-4-methoxynaphthalene and 2-(11-tetrahydropyran-2-yloxyundeca-4,9-diynyl)-1-(tetrahydropyran-2-yloxy)-4-methoxynaphthalene.
Claim 10
Independent Claim
104 words
A method for inhibiting or preventing the hypersecretion of mucus in the respiratory tract of a mammal in need thereof which comprises administering to said patient a compound of Formula I ##STR3## wherein R 1 is tetrahydro-2H-pyranyl, --C(O)CH 3 , the residue of an amino acid having the structure --C(O)--CH-(isopropyl)-NH 2 , the N-t-butylcarbonyloxy derivative or the HCl salt thereof, or --C(O)--(CH 2 ) 2 --COOH or a pharmaceutically acceptable salt thereof; R 2 is --C.tbd.C--(CH 2 ) m --C.tbd.C--(CH 2 ) p --OR 1 and n is 3 or 4, m is 1 to 5, inclusive and p is 0 to 3 inclusive.
Claim 11
Independent Claim
104 words
A method for inhibiting or preventing the hypersecretion of mucus in the respiratory tract of a mammal in need thereof which comprises administering to said patient a compound of Formula I ##STR3## wherein R 1 is tetrahydro-2H-pyranyl, --C(O)CH 3 , the residue of an amino acid having the structure --C(O)--CH-(isopropyl)-NH 2 , the N-t-butylcarbonyloxy derivative or the HCl salt thereof, or --C(O)--(CH 2 ) 2 --COOH or a pharmaceutically acceptable salt thereof; R 2 is --C.tbd.C--(CH 2 ) m --C.tbd.C--(CH 2 ) p --OR 1 and n is 3 or 4, m is 1 to 5, inclusive and p is 0 to 3 inclusive.
References Cited (Backward Citations)
US4407757B1
Cited
US4407757A
Cited
US4102902A
Cited
US4388312A
Cited
JPS56140943A
Cited
JPS57120519A
Cited
JPS57128624A
Cited
JPS5883698A
Cited
JPS58174343A
Cited
DE3311922A1
Cited
JPS58174342A
Cited
EP0092136A1
Cited
EP0103361A1
Cited
JPS5910541A
Cited
EP0106341A2
Cited
EP0124379A1
Cited
JPS6075442A
Cited
EP0146348A2
Cited
EP0201071A2
Cited
US4833164A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-07-02 | 1994-01-01 | 1994-07-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-07-02 | 1998-01-01 | 1998-07-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-07-02 | 2002-01-01 | 2002-07-03 | $7700.00 | Window Closed / Lapsed |