US4720500A
Expired / Lapsed
US
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N-1,8-naphthyridin-2-yl amides useful as immunostimulants
Assignee: Rhone Poulenc Sante SA
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Filing: 1986-07-10
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Granted: 1988-01-19
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Expires: 2006-07-10
Abstract
Abstract Amides of formula ##STR1## in which either R is 2-quinolyl, substituted phenyl (substituted by Br, 3-Cl, CF 3 , alkyloxycarbonyl, 4-dialkylamino), dichlorophenyl, trialkyloxyphenyl, benzyl, styryl, benzoyl or anilino and R' is halogen, phenyl or anilino or R' is phenoxy or 4-chlorophenoxy when R is 2-quinolyl, substituted phenyl, trialkyloxyphenyl, benzyl or styryl or R' is 4-fluoro(or alkyloxy)phenyl when R is 4-trifluoromethyl (or dialkylamino)phenyl, or R' is 3-bromophenyl when R is anilino, or R is phenyl or alkyloxyphenyl and R' is phenyl, 4-chlorophenoxy, anilino or 1-pyrrolidinyl or R' is 2-(or 4-)chlorophenyl, 3-(or 4-)bromophenyl, 4-alkyloxyphenyl or 3,4-dichloro(or dibromo)phenyl when R is phenyl or R is 3-halophenyl and R' is 3-(or 4-)fluorophenyl, 3-(or 4-)bromophenyl, 4-chlorophenyl, 2-(or 3-)-alkyloxyphenyl, 3-alkylphenyl or 3,4-difluoro(dichloro or dibromo)phenyl, the straight-chain or branched alkyl radical containing 1 to 4 carbon atoms each, are useful as immunostimulant agents. The invention also provides processes for their preparation and pharmaceutical compositions containing them.
Inventors
- 👤 Claude Cotrel
- 👤 Claude Guyon
- 👤 Gerard Roussel
- 👤 Gerard Taurand
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 04:19
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
167 words
A substituted amide of the formula: ##STR6## in which either: (1) R represents 2-quinolyl, substituted phenyl (the substituent being bromine, chlorine in position -3, trifluoromethyl, alkyloxycarbonyl, or dialkylamino in position -4), dichlorophenyl, trialkyloxyphenyl, benzyl, styryl, benzoyl or anilino, and R' represents halogen, phenyl, anilino, or R' represents phenoxy or 4-chlorophenoxy when R is 2-quinolyl, substituted phenyl (the substituent being bromine, chlorine in position -3, trifluoromethyl, alkyloxycarbonyl, or dialkylamino in position -4), trialkyloxyphenyl, benzyl or styryl, or R' represents 4-fluorophenyl or 4-alkyloxyphenyl when R is 4-trifluoromethylphenyl or 4-dialkylaminophenyl, or R' represents 3-bromophenyl when R is anilino, or (2) R represents phenyl or alkyloxyphenyl and R' represents phenyl, 4-chlorophenoxy, anilino or 1-pyrrolidinyl, or R' represents 2-(or 4-)chlorophenyl, 3-(or 4-)bromophenyl, 4-alkyloxyphenyl or 3,4-dichloro(or dibromo)phenyl when R is phenyl, or (3) R represents phenyl substituted by halogen in position -3 and R' represents 3-(or 4-)fluorophenyl, 3-(or 4-)bromophenyl, 4-chdlorophenyl, 2-(or 3-)alkyloxyphenyl, 3-alkylphenyl, or 3,4-difluoro(dichloro or dibromo)phenyl: the aforesaid alkyl radicals being straight-chain or branched and containing 1 to 4 carbon atoms each.
Claim 2
Dependent Claim
167 words
A substituted amide of the formula: ##STR6## in which either: (1) R represents 2-quinolyl, substituted phenyl (the substituent being bromine, chlorine in position -3, trifluoromethyl, alkyloxycarbonyl, or dialkylamino in position -4), dichlorophenyl, trialkyloxyphenyl, benzyl, styryl, benzoyl or anilino, and R' represents halogen, phenyl, anilino, or R' represents phenoxy or 4-chlorophenoxy when R is 2-quinolyl, substituted phenyl (the substituent being bromine, chlorine in position -3, trifluoromethyl, alkyloxycarbonyl, or dialkylamino in position -4), trialkyloxyphenyl, benzyl or styryl, or R' represents 4-fluorophenyl or 4-alkyloxyphenyl when R is 4-trifluoromethylphenyl or 4-dialkylaminophenyl, or R' represents 3-bromophenyl when R is anilino, or (2) R represents phenyl or alkyloxyphenyl and R' represents phenyl, 4-chlorophenoxy, anilino or 1-pyrrolidinyl, or R' represents 2-(or 4-)chlorophenyl, 3-(or 4-)bromophenyl, 4-alkyloxyphenyl or 3,4-dichloro(or dibromo)phenyl when R is phenyl, or (3) R represents phenyl substituted by halogen in position -3 and R' represents 3-(or 4-)fluorophenyl, 3-(or 4-)bromophenyl, 4-chdlorophenyl, 2-(or 3-)alkyloxyphenyl, 3-alkylphenyl, or 3,4-difluoro(dichloro or dibromo)phenyl: the aforesaid alkyl radicals being straight-chain or branched and containing 1 to 4 carbon atoms each.
Claim 3
Dependent Claim
125 words
An amide according to claim 1, wherein either: (1) R represents 2-quinolyl, 4-dialkylaminophenyl, dichlorophenyl, trialkyloxyphenyl, benzyl, styryl or benzoyl, and R' represents chlorine or phenyl, or R' represents phenoxy when R is bromophenyl, or R' represents chlorine when R is bromophenyl, trifluoromethylphenyl or anilino, or R' represents 3-bromophenyl when R is anilino, or (2) R represents phenyl or alkyloxyphenyl and R' represents phenyl, 4-chlorophenoxy, anilino or 1-pyrrolidinyl, or R' represents 2-(or 4-)chlorophenyl, 3-(or 4-)bromophenyl, or 4-alkyloxyphenyl when R is phenyl, or (3) R represents phenyl substituted in the 3-position by a halogen atom and R' represents 3-(or 4-)fluorophenyl, 3-(or 4-)bromophenyl, 4-chlorophenyl, 2-(or 3-)alkyloxyphenyl, 3-alkylphenyl or 3,4-difluoro(or dichloro or dibromo)phenyl, the aforesaid alkyl radicals being straight-chain or branched and containing 1 to 4 carbon atoms each.
Claim 4
Dependent Claim
10 words
The substituted amide according to claim 1 which is N-(7-phenyl-1,8-naphthyridin-2-yl)-3-bromobenzamide.
Claim 5
Dependent Claim
10 words
The substituted amide according to claim 1 which is N-(7-phenyl-1,8-naphthyridin-2-yl)-4-methoxybenzamide.
Claim 6
Dependent Claim
10 words
The substituted amide according to claim 1 which is N-(7-(1-pyrrolidinyl)-1,8-naphthyridin-2-yl)-benzamide.
Claim 7
Dependent Claim
10 words
The substituted amide according to claim 1 which is N-(7-(4-chlorophenyl)-1,8-naphthyridin-2-yl)-3-bromobenzamide.
Claim 8
Dependent Claim
10 words
The substituted amide according to claim 1 which is N-(7-(4-fluorophenyl)-1,8-naphthyridin-2-yl)-3-bromobenzamide.
Claim 9
Dependent Claim
30 words
A pharmaceutical composition useful as an immunostimulant comprising an effective amount of an amide according to claim 1 in combination with one or more compatible, pharmaceutically acceptable diluents or adjuvants.
References Cited (Backward Citations)
US4086348A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-01-18 | 1991-07-20 | 1992-01-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-01-18 | 1995-07-20 | 1996-01-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-01-18 | 1999-07-20 | 2000-01-19 | $7700.00 | Window Closed / Lapsed |