Claims
- 1. A compound of structural formula: ##STR24## or a pharmaceutically acceptable salt thereof wherein m is 0 or 1;
- A is ##STR25## where R.sup.7 is hydrogen, chloro or fluoro; R.sup.1 and R.sup.2 are independently hydrogen or C.sub.1-3 alkyl;
- R.sup.3 is
- (a) SO.sub.3 H;
- (b) PO.sub.3 H.sub.2 ; ##STR26## (d) ethoxycarbonylmethyl; ##STR27## where E represents (1) phenyl;
- (2) 2-acetoxyphenyl;
- (3) 2-hydroxy-4-(2,4-difluorophenyl)phenyl;
- (4) 3-chloro-4-allyloxybenzyl;
- (5) .alpha.-methyl-4-isobutylbenzyl;
- (6) .alpha.-methyl-3-phenoxybenzyl;
- (7) .alpha.-methyl-3-benzoylbenzyl;
- (8) 1-(6-methoxynaphth-2-yl)ethyl;
- (9) .alpha.-methyl-3-fluoro-4-phenylbenzyl;
- (10) 2-(3-chloro-4-cyclohexylbenzoyl)ethyl;
- (11) 2-(3-trifluoromethylanilino)phenyl;
- (12) 2-(2,3-dimethylanilino)phenyl;
- (13) 2-(2,6-dichloro-3-methylanilino)phenyl;
- (14) 2-(3-trifluoromethylanilino-3-pyridyl; or
- (15) 2-(2-methyl-3-chloroanilino)-3-pyridyl; ##STR28## R.sup.4 is (a) hydrogen; or
- (b) C.sub.1-3 alkyl;
- R is
- (a) hydroxy; or
- (b) hydroxy-C.sub.1-3 alkyl.
- 2. The compound of the structural formula ##STR29## or a pharmaceutically acceptable salt thereof, where R is --OH and E is phenyl, 2-acetoxyphenyl, 2-hydroxy-4-(2,4-difluorophenyl)phenyl, 3-chloro-4-allyloxybenzyl, .alpha.-methyl-4-isobutylbenzyl, .alpha.-methyl-3-phenoxybenzyl, .alpha.-methyl-3-benzoylbenzyl, 1-(6-methoxynaphth-2-yl)ethyl, .alpha.-methyl-3-fluoro-4-phenylbenzyl, 2-(3-chloro-4-cyclohexylbenzoyl)ethyl, 2-(3-trifluoromethylanilino)phenyl, 2-(2,3-dimethylanilino)phenyl, 2-(2,6-dichloro-3-methylanilino)phenyl, 2-(3-trifluoromethylanilino)-3-pyridyl, or 2-(2-methyl-3-chloroanilino)-3-pyridyl.
- 3. The compound of the formula: ##STR30## or pharmaceutically acceptable salt thereof, wherein L is --(CH.sub.2).sub.1-5, phenylene, or ##STR31##
- 4. A pharmaceutical anti-inflammatory composition in unit dosage form comprising a pharmaceutically acceptable inert carrier and an effective amount of a compound having the structural formula: ##STR32## or a pharmaceutically acceptable salt thereof wherein m is 0 or 1;
- A is ##STR33## where R.sup.7 is hydrogen, chloro or fluoro; R.sup.1 and R.sup.2 are independently hydrogen or C.sub.1-3 alkyl;
- R.sup.3 is
- (a) SO.sub.3 H;
- (b) PO.sub.3 H.sub.2 ; ##STR34## (d) ethoxycarbonylmethyl; ##STR35## where E represents (1) phenyl;
- (2) 2-acetoxyphenyl;
- (3) 2-hydroxy-4-(2,4-difluorophenyl)phenyl;
- (4) 3-chloro-4-allyloxybenzyl;
- (5) .alpha.-methyl-4-isobutylbenzyl;
- (6) .alpha.-methyl-3-phenoxybenzyl;
- (7) .alpha.-methyl-3-benzoylbenzyl;
- (8) 1-(6-methoxynaphth-2-yl)ethyl;
- (9) .alpha.-methyl-3-fluoro-4-phenylbenzyl;
- (10) 2-(3-chloro-4-cyclohexylbenzoyl)ethyl;
- (11) 2-(3-trifluoromethylanilino)phenyl;
- (12) 2-(2,3-dimethylanilino)phenyl;
- (13) 2-(2,6-dichloro-3-methylanilino)phenyl;
- (14) 2-(3-trifluoromethylanilino-3-pyridyl; or
- (15) 2-(2-methyl-3-chloroanilino)-3-pyridyl; ##STR36## R.sup.4 is (a) hydrogen; or
- (b) C.sub.1-3 alkyl;
- R is
- (a) hydroxy; or
- (b) hydroxy-C.sub.1-3 alkyl.
- 5. The pharmaceutical composition of claim 4 wherein the compound is of formula ##STR37## or a pharmaceutically acceptable salt thereof, where R is --OH and E is phenyl, 2-acetoxy-phenyl, 2-hydroxy-4-(2,4-difluorophenyl)phenyl, 3-chloro-4-allyloxybenzyl, .alpha.-methyl-4-isobutylbenzyl, .alpha.-methyl-3-phenoxybenzyl, .alpha.-methyl-3-benzoylbenzyl, 1-(6-methoxynaphth-2-yl)ethyl, .alpha.-methyl-3-fluoro-4-phenylbenzyl, 2-(3-chloro-4-cyclohexylbenzoyl)ethyl, 2-(3-trifluoromethylanilino)phenyl, 2-(2,3-dimethylanilino)phenyl, 2-(2,6-dichloro-3-methylanilino)phenyl, 2-(3-trifluoromethylanilino)-3-pyridyl, or 2-(2-methyl-3-chloroanilino)-3-pyridyl.
- 6. A pharmaceutical composition in unit dosage form comprising a pharmaceutically acceptable inert carrier and an effective amount of a compound having the following structural formula ##STR38## or a pharmaceutically acceptable salt thereof, wherein L is --(CH.sub.2).sub.1-5, phenylene, or ##STR39##
- 7. A method of treating inflammation which comprises the administration to a warm-blooded animal or human in need of such treatment an effective amount of a compound having the structural formula ##STR40## or a pharmaceutically acceptable salt thereof wherein m is 0 or 1;
- A is ##STR41## where R.sup.7 is hydrogen, chloro or fluoro; R.sup.1 and R.sup.2 are independently hydrogen or C.sub.1-3 alkyl;
- R.sup.3 is
- (a) SO.sub.3 H;
- (b) PO.sub.3 H.sub.2 ; ##STR42## (d) ethoxycarbonylmethyl; ##STR43## where E represents (1) phenyl;
- (2) 2-acetoxyphenyl;
- (3) 2-hydroxy-4-(2,4-difluorophenyl)phenyl;
- (4) 3-chloro-4-allyloxybenzyl;
- (5) .alpha.-methyl-4-isobutylbenzyl;
- (6) .alpha.-methyl-3-phenoxybenzyl;
- (7) .alpha.-methyl-3-benzoylbenzyl;
- (8) 1-(6-methoxynaphth-2-yl)ethyl;
- (9) .alpha.-methyl-3-fluoro-4-phenylbenzyl;
- (10) 2-(3-chloro-4-cyclohexylbenzoyl)ethyl;
- (11) 2-(3-trifluoromethylanilino)phenyl;
- (12) 2-(2,3-dimethylanilino)phenyl;
- (13) 2-(2,6-dichloro-3-methanilino)phenyl;
- (14) 2-(3-trifluoromethylanilino-3-pyridyl; or
- (15) 2-(2-methyl-3-chloroanilino)-3-pyridyl; ##STR44## R.sup.4 is (a) hydrogen; or
- (b) C.sub.1-3 alkyl;
- R is
- (a) hydroxy;
- (b) hydroxy-C.sub.1-3 alkyl.
- 8. The method of claim 7 wherein the compound is of formula ##STR45## or a pharmaceutically acceptable salt thereof, where R is --OH and E is phenyl, 2-acetoxy-phenyl, 2-hydroxy-4-(2,4-difluorophenyl)phenyl, 3-chloro-4-allyloxybenzyl, .alpha.-methyl-4-isobutylbenzyl, .alpha.-methyl-3-phenoxybenzyl, .alpha.-methyl-3-benzoylbenzyl, 1-(6-methoxynaphth-2-yl)ethyl, .alpha.-methyl-3-fluoro-4-phenylbenzyl, 2-(3-chloro-4-cyclohexylbenzoyl)ethyl, 2-(3-trifluoromethylanilino)phenyl, 2-(2,3-dimethylanilino)phenyl, 2-(2,6-dichloro-3-methylanilino)phenyl, 2-(3-trifluoromethylanilino)-3-pyridyl, or 2-(2-methyl-3-chloroanilino)-3-pyridyl.
- 9. A method of treating inflammation which comprises the administration to a warm-blooded animal or human in need of such treatment an effective amount of a compound having structural formula ##STR46## or a pharmaceutically acceptable salt thereof, wherein L is --(CH.sub.2).sub.1-5, phenylene, or ##STR47##
Parent Case Info
This is a division of application Ser. No. 010,099 filed Feb. 7, 1979, now U.S. Pat. No. 4,217,352, which in turn was a division of application Ser. No. 842,692, filed Oct. 17, 1977, now U.S. Pat. No. 4,144,342, which in turn was a division of application Ser. No. 706,033, filed July 16, 1976, now U.S. Pat. No. 4,061,759, which in turn was a division of application Ser. No. 578,692, filed May 19, 1975, now abandoned, which in turn was a continuation-in-part of application Ser. No. 464,011 filed Apr. 26, 1974, now abandoned, which in turn was a continuation-in-part of application Ser. No. 368,772, filed June 15, 1973, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3010966 |
Zima et al. |
Nov 1961 |
|
3515726 |
Haugwitz |
Jun 1970 |
|
Divisions (4)
|
Number |
Date |
Country |
Parent |
10099 |
Feb 1979 |
|
Parent |
842692 |
Oct 1977 |
|
Parent |
706033 |
Jul 1976 |
|
Parent |
578692 |
May 1975 |
|
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
464011 |
Apr 1974 |
|
Parent |
368772 |
Jun 1973 |
|