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US4866061A
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Aryl-substituted naphthyridine and pyridopyrazine derivatives
Assignee: Merck Sharp & Dohme LLC
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Filing: 1988-05-12
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Granted: 1989-09-12
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Expires: 2008-05-12
Abstract
Abstract Aryl-substituted naphthyridines and pyridopyrazines are disclosed which are useful in treating allergic reactions, inflammation, peptic ulcers and/or hyperproliferative skin disease. Pharmaceutical compositions and methods of treatment employing such compounds are also disclosed.
Inventors
- 👤 David J. Blythin
- 👤 Ho-Jane Shue
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 14:27
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; C07D471/12; C07D471/14; C07D495/00; C07D495/12; C07D495/14
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
343 words
A compound having the structural formula ##STR22## and pharmaceutically acceptable salts thereof, wherein: X represents CH or N; A represents O or S; m is an integer of from 0 to 2; n is an integer of from 0 to 2; R 1 and R 2 are the same or different and each is independently selected from H or alkyl containing 1 to 6 carbon atoms; W represents a covalent bond; B represents alkylene having from 2 to 8 carbon atoms, which alkylene may be optionally substituted with a group selected from -OH, -F, alkyl having from 1 to 4 carbon atoms, --CH 2 OH, --CHO, --CO 2 H, --COR 3 , {wherein R 3 is selected from --NHR 4 , --N(R 4 ) 2 , or --OR 4 and R 4 is alkyl of 1 to 6 carbon atoms}, or --CN; Q represents an aryl group containing from 6 to 15 carbon atoms or an aromatic heterocyclic group containing from 3 to 14 carbon atoms and having at least one O, S, or N in the ring, which aryl or aromatic heterocyclic group can optionally be substituted with up to 3 substituents Y as defined below; and each Y substituent is independently selected form --OH, hydroxymethyl, alkyl containing from 1 to 6 carbon atoms, halo, --N 2 , alkoxy containing 1 to 6 carbon atoms, --CF 3 , --CN, cycloalkyl containing 3 to 7 carbon atoms, alkenyloxy containing from 3 to 6 carbon atoms, alkynyloxy containing from 3 to 6 carbon atoms, --S(O) p -R 4 , {wherein R 4 is as defined above and p is an integer of from 0 to 2}, --CO--R 5 {wherein R 5 represents --OH, --NH 2 , --NHR 4 , --N(R 4 ) 2 or --OR 4 in which R 4 is as defined above}, --O--D--COR 5 , {wherein D represents alkylene having from 1 to 4 carbon atoms and R 5 is a defined above}, --NH 2 , --NHR 4 , --H(R 4 ) 2 {wherein R.sup. 4 is as defined above} or --NHCOH.
Claim 2
Dependent Claim
343 words
A compound having the structural formula ##STR22## and pharmaceutically acceptable salts thereof, wherein: X represents CH or N; A represents O or S; m is an integer of from 0 to 2; n is an integer of from 0 to 2; R 1 and R 2 are the same or different and each is independently selected from H or alkyl containing 1 to 6 carbon atoms; W represents a covalent bond; B represents alkylene having from 2 to 8 carbon atoms, which alkylene may be optionally substituted with a group selected from -OH, -F, alkyl having from 1 to 4 carbon atoms, --CH 2 OH, --CHO, --CO 2 H, --COR 3 , {wherein R 3 is selected from --NHR 4 , --N(R 4 ) 2 , or --OR 4 and R 4 is alkyl of 1 to 6 carbon atoms}, or --CN; Q represents an aryl group containing from 6 to 15 carbon atoms or an aromatic heterocyclic group containing from 3 to 14 carbon atoms and having at least one O, S, or N in the ring, which aryl or aromatic heterocyclic group can optionally be substituted with up to 3 substituents Y as defined below; and each Y substituent is independently selected form --OH, hydroxymethyl, alkyl containing from 1 to 6 carbon atoms, halo, --N 2 , alkoxy containing 1 to 6 carbon atoms, --CF 3 , --CN, cycloalkyl containing 3 to 7 carbon atoms, alkenyloxy containing from 3 to 6 carbon atoms, alkynyloxy containing from 3 to 6 carbon atoms, --S(O) p -R 4 , {wherein R 4 is as defined above and p is an integer of from 0 to 2}, --CO--R 5 {wherein R 5 represents --OH, --NH 2 , --NHR 4 , --N(R 4 ) 2 or --OR 4 in which R 4 is as defined above}, --O--D--COR 5 , {wherein D represents alkylene having from 1 to 4 carbon atoms and R 5 is a defined above}, --NH 2 , --NHR 4 , --H(R 4 ) 2 {wherein R.sup. 4 is as defined above} or --NHCOH.
Claim 3
Dependent Claim
17 words
A pharmaceutical composition comprising a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 4
Dependent Claim
31 words
A method of treating an allergic reaction in a mammal comprising administering a compound of formula I as defined in claim 1 in an amount effective to treat an allergic reaction.
Claim 5
Dependent Claim
27 words
A method of treating infammation in a mammal comprising administering to said an antiinflammatory effective amount of a compound of formula I as defined in claim 1.
Claim 6
Dependent Claim
30 words
A method of treating a peptic ulcer in a mammal comprising administering to said mammal a cytoprotective effective amount of a compound of formula I as defined in claim 1.
Claim 7
Dependent Claim
32 words
A method of treating hyperproliferative skin disease in a mammal comprising administering to said mammal and anti-hyperproliferative skin disease effective amount of a compound of formula I as defined in claim 1.
Claim 8
Dependent Claim
16 words
A method according to claim 6 wherein the disease is psoriasis, lichenfied eczema or seborrheic dermatitis.
Claim 9
Dependent Claim
11 words
A method according to claim 7 wherein the disease is psoriasis.
Claim 10
Dependent Claim
12 words
A compound according to claim 1 selected from: 5-phenyl-7,8,9,10-tetrahydro-benzo-naphthyridin-6(5H)-one; 5-(3-chlorophenyl)-7,8,9,10-tetrahydro-benzo-naphthyridin-6(5H)-one; or 1,2-dihydro-2-(hydroxymethyl)-4-phenylcyclobuta(c)-naphthyridin-3(4H)-one.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1992-09-11 | 1993-03-13 | 1993-09-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-09-11 | 1997-03-13 | 1997-09-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-09-11 | 2001-03-13 | 2001-09-12 | $7700.00 | Window Closed / Lapsed |