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Claims for Patent: 3,725,548

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Claims for Patent: 3,725,548

Title: SUBSTITUTED INDENYL ACETIC ACIDS IN THE TREATMENT OF PAIN, FEVER OR INFLAMMATION
Abstract:New substituted indenyl acetic acids and nontoxic pharmaceutically acceptable amides, esters and salts derived therefrom. The substituted indenyl acetic acids disclosed herein have anti-inflammatory, anti-pyretic and analgesic activity. Also included herein are methods of preparing said indenyl acetic acid compounds, pharmaceutical compositions having said indenyl acetic acid compounds as an active ingredient and methods of treating inflammation by administering these particular compositions to patients.
Inventor(s): Shen; Tsung-Ying (Westfield, NJ), Greenwald; Richard B. (Framingham, MA), Jones; Howard (Holmdel, NJ), Linn; Bruce O. (Somerville, NJ), Witzell; Bruce E. (Westfield, NJ)
Assignee: Merck & Co., Inc. (Rahway, NJ)
Application Number:05/187,197
Patent Claims: 1. A method of treating pain, fever or inflamation which comprises administering to a host a therapeutically effective amount of a compound. ##SPC4##

wherein:

R.sub.1 is hydrogen, loweralkyl or halogenated loweralkyl;

R.sub.2 is hydrogen or alkyl;

R.sub.3, r.sub.4, r.sub.5 and R.sub.6 each are hydrogen, loweralkyl, loweralkoxy, nitro, amino, loweralkylamino, lowerdialkylamino, lowerdialkylaminoloweralkyl, sulfamyl, loweralkylthio, mercapto, hydroxy, hydroxyloweralkyl, loweralkylsulfonyl, cyano, halogen, carboxyl, carbloweralkyl, carbamido, halogenoalkyl, cycloalkyl, or cycloalkoxy;

R.sub.7 is alkylsulfinyl or alkylsulfonyl;

R.sub.8 is hydrogen, ahalogen, hydroxy, alkoxy or haloalkyl; and

M is hydroxy, loweralkoxy, benzyloxy, phenoxy, or the group OMe wherein

Me is alkali metal or alkali earth metal.

2. A method of treating pain, fever, or inflamation in accordance with the method of claim 1 wherein the compound is of the formula: ##SPC5##

wherein:

R.sub.1 is hydrogen, loweralkyl, or haloloweralkyl;

R.sub.2 is hydrogen or loweralkyl;

R.sub.3 is hydrogen;

R.sub.4 is hydrogen, halogen, loweralkoxy, amino, loweralkylamino or diloweralkylamino;

R.sub.5 is hydrogen, halogen, loweralkoxy, amino, loweralkylamino, or diloweralkylamino;

R.sub.6 is hydrogen, halogen, loweralkoxy, amino, loweralkylamino or diloweralkylamino;

R.sub.7 is loweralkylsulfinyl or loweralkylsulfonyl;

R.sub.8 is hydrogen, halogen, hydroxy, loweralkoxy, loweralkyl or haloloweralkyl; and

M is hydroxy, loweralkoxy, benzyloxy, phenoxy, or the group OMe wherein

Me is alkali metal or alkali earth metal.

3. A method of treating pain, fever, or inflamation in accordance with the method of claim 1 wherein the compound is of the formula: ##SPC6##

wherein:

R.sub.1 is hydrogen or loweralkyl;

R.sub.2 is loweralkyl;

R.sub.3 is hydrogen;

R.sub.4 is halogen, loweralkyoxy, or diloweralkylamino;

R.sub.5 is hydrogen, halogen, loweralkoxy or diloweralkylamino;

R.sub.6 is hydrogen, halogen, loweralkoxy or diloweralkylamino;

R.sub.7 is loweralkylsulfinyl or loweralkylsulfonyl; and

R.sub.8 is hydrogen.

4. The method of claim 1 wherein the compound is 5,6-difluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

5. The method of claim 1 wherein the compound is 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

6. The method of claim 1 wherein the compound is .alpha.-[5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl]-prop ionic acid.

7. The method of claim 1 wherein the compound is 5,7-difluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

8. The method of claim 1 wherein the compound is 5-chloro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

9. The method of claim 1 wherein the compound is 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

10. A method of treating pain, fever, or inflamation which comprises administering to a host a therapeutically effective amount of cis-5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

11. A pharmaceutical composition for the treatment of pain, fever or inflammation comprising an effective amount of a compound of the formula ##SPC7##

wherein:

R.sub.1 is hydrogen, loweralkyl or halogenated loweralkyl;

R.sub.2 is hydrogen or alkyl;

R.sub.3, r.sub.4, r.sub.5 and R.sub.6 each are hydrogen, loweralkyl, loweralkoxy, nitro, amino, loweralkylamino, lowerdialkylamino, lowerdialkylaminoloweralkyl, sulfamyl, loweralkylthio, mercapto, hydroxy, hydroxyloweralkyl, loweralkylsulfonyl, halogen, carboxyl, carbloweralkoxy, carbamido, halogenoalkyl, cycloalkyl, or cycloalkoxy;

R.sub.7 is alkylsulfinyl or alkylsulfonyl;

R.sub.8 is hydrogen, halogen, hydroxy, alkoxy or haloalkyl; and

M is hydroxy, loweralkoxy, benzyloxy, phenoxy, or the group OMe wherein

Me is alkali metal or alkali earth metal and a pharmaceutically acceptable carrier therefore.

12. A pharmaceutical composition as in claim 11 wherein the active ingredient is a compound selected from the formula: ##SPC8##

wherein:

R.sub.1 is hydrogen, loweralkyl, or haloloweralkyl;

R.sub.2 is hydrogen or loweralkyl;

R.sub.3 is hydrogen;

R.sub.4 is hydrogen, halogen, loweralkoxy, amino, loweralkylamino or diloweralkylamino;

R.sub.5 is hydrogen, halogen, loweralkoxy, amino, loweralkylamino, or diloweralkylamino;

R.sub.6 is hydrogen, halogen, loweralkoxy, amino, loweralkylamino or diloweralkylamino;

R.sub.7 is loweralkylsulfinyl or loweralkylsulfonyl;

R.sub.8 is hydrogen, halogen, hydroxy, loweralkoxy, loweralkyl or haloloweralkyl; and

M is hydroxy, loweralkoxy, benzyloxy, phenoxy, or the group OMe wherein

Me is alkali metal or alkali earth metal.

13. A pharmaceutical composition as in claim 12 wherein the active ingredient is a compound of the formula: ##SPC9##

wherein:

R.sub.1 is hydrogen or loweralkyl;

R.sub.2 is loweralkyl;

R.sub.3 is hydrogen;

R.sub.4 is halogen, loweralkoxy, or diloweralkylamino;

R.sub.5 is hydrogen, halogen, loweralkoxy or diloweralkylamino;

R.sub.6 is hydrogen, halogen, loweralkoxy or diloweralkylamino;

R.sub.7 is loweralkylsulfinyl or loweralkylsulfonyl; and

R.sub.8 is hydrogen.

14. A pharmaceutical composition as in claim 13 wherein the compound is 5,6-difluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

15. A pharmaceutical composition as in claim 14 wherein the compound is 5-fluoro-2-methyl-1-(p-methylsulfinyl-benzylidene)-3-indene acetic acid.

16. A pharmaceutical composition as in claim 15 wherein the compound is .alpha.-[5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indenyl]-prop ionic acid.

17. A pharmaceutical composition as in claim 16 wherein the compound is 5,7-difluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

18. A pharmaceutical composition as in claim 17 wherein the compound is 5 -chloro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

19. A pharmaceutical composition as in claim 18 wherein the compound is 6-fluoro-5-methoxy-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.

20. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and cis-5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-3-indene acetic acid.
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