US4346105A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Novel substituted phenylacetic acid amide compounds
Assignee: Novartis Corp
•
Filing: 1980-12-17
•
Granted: 1982-08-24
•
Expires: 2000-12-17
Abstract
Abstract Phenylacetic acid amide compounds of the formula ##STR1## in which R 1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R 2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R 3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R 4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R 5 is a radical of aliphatic character containing the group R 6 , R 6 and R 7 are each hydrogen or together are a divalent aliphatic radical and the group of the formula --C(═O)--R 8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.
Inventors
- 👤 Alfred Sallmann
- 👤 Gerhard Baschang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 19:14
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/02; C07K5/0202; A; A61; A61K; A61K38/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
242 words
A compound of the formula ##STR14## in which R 1 is lower alkyl having not more than 4 carbon atoms or halogen having an atomic number of not more than 35, R 2 ' is hydrogen, lower alkyl having not more than 4 carbon atoms or halogen having an atomic number of not more than 35 and R 3 is hydrogen, with the proviso that R 3 ' can also be lower alkyl having not more than 4 carbon atoms, in the 3-position, if R 1 ' is one of the said halogen atoms and R 2 ' is hydrogen, or with the proviso that R 3 ' can also be halogen having an atomic number of not more than 35, in the 4-position, if R 1 ' is one of said halogen atoms and R 2 ' is hydrogen, and R 5 ' is lower alkyl having not more than 4 carbon atoms substituted by hydroxyl or lower alkoxy, and R 8 ' is hydroxyl, lower alkoxy having not more than 4 carbon atoms or substituted or unsubstituted amino, substituted amino being a radical of the formula --NH--CH(R 5 a' )--C(═O)--R 8 a' , in which R 5 a' , and R 8 a' have the meanings for R 5 ' and R 8 ' respectively, and a radical of the formula --NH--CH(R 5 ')--C(═O)--R 8 ' consisting of one, two or three aminoacid radicals, or a therapeutically acceptable salt thereof.
Claim 2
Dependent Claim
242 words
A compound of the formula ##STR14## in which R 1 is lower alkyl having not more than 4 carbon atoms or halogen having an atomic number of not more than 35, R 2 ' is hydrogen, lower alkyl having not more than 4 carbon atoms or halogen having an atomic number of not more than 35 and R 3 is hydrogen, with the proviso that R 3 ' can also be lower alkyl having not more than 4 carbon atoms, in the 3-position, if R 1 ' is one of the said halogen atoms and R 2 ' is hydrogen, or with the proviso that R 3 ' can also be halogen having an atomic number of not more than 35, in the 4-position, if R 1 ' is one of said halogen atoms and R 2 ' is hydrogen, and R 5 ' is lower alkyl having not more than 4 carbon atoms substituted by hydroxyl or lower alkoxy, and R 8 ' is hydroxyl, lower alkoxy having not more than 4 carbon atoms or substituted or unsubstituted amino, substituted amino being a radical of the formula --NH--CH(R 5 a' )--C(═O)--R 8 a' , in which R 5 a' , and R 8 a' have the meanings for R 5 ' and R 8 ' respectively, and a radical of the formula --NH--CH(R 5 ')--C(═O)--R 8 ' consisting of one, two or three aminoacid radicals, or a therapeutically acceptable salt thereof.
Claim 3
Dependent Claim
149 words
A compound according to claim 1 in which R 1 ' and R 2 ' are each chlorine and R 3 ' is hydrogen, or R 1 ' is chlorine, R 2 ' is hydrogen and R 3 ' is methyl in the 3-position or chlorine in the 4-position, and R 5 ' is hydrogen or lower alkyl having not more than 4 carbon atoms which is unsubstituted or substituted by hydroxy or lower alkoxy, and R 8 ' is hydroxy, lower alkoxy, amino or substituted amino, substituted amino being a radical of the formula --NH--CH(R 5 a' )--C(═O)--R 8 a' , in which R 5 a' and R 8 a' have the meanings defined for R 5 ' and R 8 ' respectively, and a radical of the formula --NH--CH(R 5 ')--C(═O)--R 8 ' consisting of one, two or three aminoacid radicals, or a therapeutically acceptable salt thereof.
Claim 4
Dependent Claim
16 words
A compound according to claim 1, in which the radical --NH--CH(R 5 ')--C(═O)-- has the D-configuration.
Claim 5
Dependent Claim
21 words
A pharmaceutical preparation containing an antiinflammatory effective amount of a compound as claimed in claim 1 together with conventional pharmaceutical excipients.
Claim 6
Dependent Claim
90 words
A compound of the formula ##STR15## in which each of R 1 and R 2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, each of R 3 and R 4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, R 5 is lower alkylene or lower alkylidene, R 6 is hydroxyl or lower alkoxy, R 7 is hydrogen and R 8 is hydroxy or lower alkoxy, or a therapeutically acceptable salt thereof.
Claim 7
Dependent Claim
90 words
A compound of the formula ##STR15## in which each of R 1 and R 2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, each of R 3 and R 4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, R 5 is lower alkylene or lower alkylidene, R 6 is hydroxyl or lower alkoxy, R 7 is hydrogen and R 8 is hydroxy or lower alkoxy, or a therapeutically acceptable salt thereof.
Claim 8
Dependent Claim
116 words
A compound as claimed in claim 5, in which formula R 1 is hydrogen, alkyl or alkoxy having not more than 4 carbon atoms each, halogen having an atomic number of not more than 35, or trifluoromethyl, each of R 2 , R 3 and R 4 are hydrogen, alkyl or alkoxy having not more than 4 carbon atoms each, or halogen having an atomic number of not more than 35, R 5 is alkylene or alkylidene having not more than 7 carbon atoms each, R 6 is hydroxyl or lower alkoxy, R 7 is hydrogen and R 8 is hydroxy or alkoxy having not more than 4 carbon atoms, or a therapeutically acceptable salt thereof.
Claim 9
Dependent Claim
187 words
A compound as claimed in claim 1 and having the formula ##STR16## in which R 1 ' is alkyl having not more than 4 carbon atoms or halogen having an atomic number of not more than 35, R 2 ' is hydrogen, alkyl having not more than 4 carbon atoms or halogen having an atomic number of not more than 35 and R 3 ' is hydrogen, with the proviso that R 3 ' can also be alkyl having not more than 4 carbon atoms, in the 3-position, if R 1 ' is one of the said halogen atoms and R 2 ' is hydrogen, or with the proviso that R 3 ' can also be halogen having an atomic number of not more than 35, in the 4-position, if R 1 ' is one of the said halogen atoms and R 2 ' is hydrogen, R 5 ' is alkyl having not more than 4 carbon atoms, which is substituted by hydroxyl or lower alkoxy, and R 8 ' is hydroxyl or alkoxy having not more than 4 carbon atoms or a therapeutically acceptable salt thereof.
Claim 10
Dependent Claim
93 words
A compound as claimed in claim 1, in which formula R 1 ' and R 2 ' are each chlorine and R 3 ' is hydrogen, or R 1 ' is chlorine, R 2 ' is hydrogen and R 3 ' is methyl in the 3-position or chlorine in the 4-position, and R 5 ' is alkyl having not more than 4 carbon atoms which is substituted by hydroxyl or lower alkoxy, and R 8 ' is hydroxyl or alkoxy having not more than 4 carbon atoms, or a therapeutically acceptable saltg thereof.
Claim 11
Dependent Claim
15 words
A compound as claimed in claim 1 being L(+)-N-{[2-(2,6-dichlorophenyl-amino)phenyl]acetyl}-serine or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
15 words
A compound as claimed in claim 1 being D-(-)-N-{[2-(2,6-dichlorophenyl-amino)-phenyl]-acetyl}-serine or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
13 words
A compound as claimed in claim 1 being the methyl ester of N-{[2-(2,6-dichlorophenyl-amino)-phenyl]acetyl}L-seryl-L-threonine.
Claim 14
Dependent Claim
13 words
A compound as claimed in claim 1 being the sodium salt of D(-)-N-{[2-(2,6-dichlorophenyl-amino)phenyl]-acetyl}-serine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-08-23 | 1986-02-22 | 1986-08-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-23 | 1990-02-22 | 1990-08-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-23 | 1994-02-22 | 1994-08-24 | $7700.00 | Window Closed / Lapsed |