US4687774A
Expired / Lapsed
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Method for suppressing the immune response
Assignee: Merck Sharp & Dohme LLC
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Filing: 1986-03-10
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Granted: 1987-08-18
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Expires: 2006-03-10
Abstract
Abstract A method and composition for suppressing the immune response are disclosed which employ an immunosuppressing effective amount of certain tricyclic naphthyridine or pyrido-pyrazine derivatives.
Inventors
- 👤 Sidney R. Smith
- 👤 Marvin I. Siegel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 09:23
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/495; A61K31/435; A61K31/44; A61K31/445; A61K31/535
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
213 words
A method of suppressing the immune response in a mammal which comprises administering to a mammal in need of such treatment an immunosuppressing effective amount of a compound having the structural formulae I, II or III: ##STR10## or pharmaceutical acceptable salt thereof, wherein n is 1 or 2; R 1 and R 2 may be combined to form a bond, or R 1 is hydrogen and R 2 is OR, halogen or NR 3 R 4 ; R is hydrogen, carboxylic acyl having from 2 to 10 carbon atoms, or carbamyl; R 3 and R 4 may be the same or different and each is independently hydrogen or alkyl having from 1 to 6 carbon atoms, or R 3 and R 4 may be combined with the nitrogen to which they are attached to form a pyrrolidino, piperidino, morpholino, or piperazino ring; R 5 is hydrogen or carboxylic acyl having from 2 to 10 carbon atoms; each X substituent is independently selected from hydroxy, alkyl having 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, nitro, halogen, trifluoromethyl, or alkyl--S(O) m having from 1 to 6 carbon atoms and wherein m is 0, 1 or 2; p is 0, 1, 2 or 3; and Y is CH or N.
Claim 2
Independent Claim
213 words
A method of suppressing the immune response in a mammal which comprises administering to a mammal in need of such treatment an immunosuppressing effective amount of a compound having the structural formulae I, II or III: ##STR10## or pharmaceutical acceptable salt thereof, wherein n is 1 or 2; R 1 and R 2 may be combined to form a bond, or R 1 is hydrogen and R 2 is OR, halogen or NR 3 R 4 ; R is hydrogen, carboxylic acyl having from 2 to 10 carbon atoms, or carbamyl; R 3 and R 4 may be the same or different and each is independently hydrogen or alkyl having from 1 to 6 carbon atoms, or R 3 and R 4 may be combined with the nitrogen to which they are attached to form a pyrrolidino, piperidino, morpholino, or piperazino ring; R 5 is hydrogen or carboxylic acyl having from 2 to 10 carbon atoms; each X substituent is independently selected from hydroxy, alkyl having 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, nitro, halogen, trifluoromethyl, or alkyl--S(O) m having from 1 to 6 carbon atoms and wherein m is 0, 1 or 2; p is 0, 1, 2 or 3; and Y is CH or N.
Claim 3
Dependent Claim
14 words
A method according to claim 1 wherein said compound is represented by formula I.
Claim 4
Dependent Claim
16 words
A method according to claim 1 wherein Y in formulae I, II and III is CH.
Claim 5
Dependent Claim
18 words
A method according to claim 1 wherein said compound is represented by formula I and Y is CH.
Claim 6
Dependent Claim
13 words
A method according to claim 4 wherein n in formula I is 1.
Claim 7
Dependent Claim
21 words
A method according to claim 4 wherein R 1 and R 2 in formula I are combined to form a bond.
Claim 8
Dependent Claim
14 words
A method according to claim 4 wherein R 1 in formula I is hydrogen.
Claim 9
Dependent Claim
14 words
A method according to claim 7 wherein R 2 in formula I is OR.
Claim 10
Dependent Claim
13 words
A method according to claim 8 wherein R in formula I is hydrogen.
Claim 11
Dependent Claim
14 words
A method according to claim 8 wherein R in formula I is carboxylic acyl.
Claim 12
Dependent Claim
13 words
A method according to claim 8 wherein R in formula I is carbamyl.
Claim 13
Dependent Claim
14 words
A method according to claim 7 wherein R 2 in formula I is halogen.
Claim 14
Dependent Claim
18 words
A method according to claim 7 wherein R 2 in formula I is NR 3 R 4 .
Claim 15
Dependent Claim
23 words
A method according to claim 1 wherein said compound is selected from 3,5-dihydro-2-(hydroxymethyl)-5-phenyl-furo(3,2-c)-1,8-naphthyridin-4(2H)-one, 5-(3-chlorophenyl)-3,5-dihydro-2-(hydroxymethyl)-furo(3,2-c)-1,8-naphthyridin-4(2H)-one, 2-(acetyloxymethyl)-3,5-dihydro-5-phenylfuro(3,2-c)-1,8-naphthyridin-4(2H)-one, 2-(acetyloxymethyl)-3,5-dihydro-5-(3-methoxyphenyl)-furo(3,2-c)-1,8-naphthyridin-4(2H)-one, 3,5-dihydro-2-(iodomethyl)-5-phenyl-furo(3,2-c)-1,8-naphthyridin-4(2H)-one, 3,5-dihydro-2-(iodomethyl)-5-(3-methoxyphenyl)furo(3,2-c)-1,8-naphthyridin-4(2H)-one, 3,5-dihydro-5-phenyl-2-(1-pyrrolidinylmethyl)furo(3,2-c)-1,8-naphthyridin-4(2H)-one, 3,5-dihydro-5-phenyl-2-(1-piperidinylmethyl)furo(3,2-c)-1,8-naphthyridin-4-(2H)-one, 2-(bromomethyl)-3,9-dihydro-9-phenyl-furo(2,3-b)-1,8-naphthyridin-4(2H)-one 3,9-dihydro-9-phenyl-2-(1-pyrrolidinylmethyl)furo(2,3-b)-1,8-naphthyridin-4(2H)-one, 2-(bromomethyl)-3,9-dihydro-9-(3-methoxyphenyl)-furo(2,3-b)-1,8-naphthyridin-4(2H)-one,
Claim 16
Dependent Claim
11 words
9-dihydro-2-(iodomethyl)-9-phenyl-furo(2,3-b)-1,8-naphthyridin-4(2H)-one 3,9-dihydro-2-methylene-9-phenylene-furo(2,3-b)-1,8-naphthyridin-4(2H)-one, 3-hydroxy-6-phenyl-2,3,4,6-tetrahydro-5H-pyrano(3,2-c)-1,8-naphthyridin-5-one, or 3-acetyloxy-6-phenyl-2,3,4,6-tetrahydro-5H-pyrano(3,2-c)-1,8-naphthyridin-5-one, or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
11 words
9-dihydro-2-(iodomethyl)-9-phenyl-furo(2,3-b)-1,8-naphthyridin-4(2H)-one 3,9-dihydro-2-methylene-9-phenylene-furo(2,3-b)-1,8-naphthyridin-4(2H)-one, 3-hydroxy-6-phenyl-2,3,4,6-tetrahydro-5H-pyrano(3,2-c)-1,8-naphthyridin-5-one, or 3-acetyloxy-6-phenyl-2,3,4,6-tetrahydro-5H-pyrano(3,2-c)-1,8-naphthyridin-5-one, or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
11 words
A method according to claim 4 wherein said compound is 3,5-dihydro-2-(hydroxymethyl)-5-phenylfuro[3,2-c]-1,8-naphthyridin-4(2H)-one.
Claim 19
Dependent Claim
11 words
A method according to claim 4 wherein said compound is 2-(acetyloxymethyl)-3,5-dihydro-5-phenylfuro[3,2-c]-1,8-naphthyridin-4(2H)-one.
Claim 20
Dependent Claim
12 words
A method according to claim 1 wherein the compound is administered orally.
Claim 21
Dependent Claim
12 words
A method according to claim 15 wherein the compound is administered orally.
References Cited (Backward Citations)
US4596809A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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