# US 4,393,079 A · Pharmaceutical compositions

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- Number: US 4,393,079 A
- Document ID: US4393079A
- Status: Granted
- Kind: A
- Application number: 05/750,684
- Filed: 1976-12-15
- Granted: 1983-07-12
- Earliest claimed: 1974-07-04
- Assignees: Beecham Group Limited
- Inventors: William G. Cole; Alexander C. Goudie; Carl J. Rose
- Web page: https://patentgrep.com/patent/US4393079A

## CPC

- C07C 49/84: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 29/143: of ketones
- C07C 45/45: by condensation
- C07C 45/46: Friedel-Crafts reactions
- C07C 45/62: by hydrogenation of carbon-to-carbon double or triple bonds
- C07C 45/64: by introduction of functional groups containing oxygen only in singly bound form
- C07C 45/71: being hydroxy groups
- C07C 49/213: containing six-membered aromatic rings
- C07C 49/215: polycyclic
- C07C 49/217: having unsaturation outside the aromatic rings
- C07C 49/223: polycyclic
- C07C 49/225: containing six-membered aromatic rings and other rings
- C07C 49/235: having unsaturation outside the aromatic rings
- C07C 49/245: containing six-membered aromatic rings
- C07C 49/248: having unsaturation outside the aromatic rings
- C07C 49/255: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 49/76: Ketones containing a keto group bound to a six-membered aromatic ring (compounds having a keto group being part of a condensed ring system and being bound to a six-membered aromatic ring C07C49/657 - C07C49/757)
- C07C 49/782: polycyclic
- C07C 49/792: containing rings other than six-membered aromatic rings
- C07C 49/794: having unsaturation outside an aromatic ring
- C07C 49/813: polycyclic
- C07C 49/83: polycyclic
- C07C 205/45: the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.

## Claims

### Claim 1

A pharmaceutical composition useful for the treatment of inflammation in humans and animals which comprises an anti-inflammatory amount of a compound of the formula ##STR16## wherein X is CO or CHOH;
Y is CO;
the dotted line represents a double bond which is present or absent;
R.sub.1 is hydrogen or methyl;
R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl or nitro; and
R.sub.3 is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, hydroxyl, trifluoromethyl, nitro, methylthio or methylsulphonyl;
in combination with a pharmaceutically acceptable carrier.

### Claim 2

A method of treating inflammation in humans and animals which comprises administering to a human or animal in need thereof an anti-inflammatory amount of a compound of the formula ##STR17## wherein X is CO or CHOH;
Y is CO;
the dotted line represents a double bond which is present or absent;
R.sub.1 is hydrogen or methyl;
R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl or nitro; and
R.sub.3 is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, hydroxyl, trifluoromethyl, nitro, methylthio or methylsulphonyl;
in combination with a pharmaceutically acceptable carrier.

### Claim 3 (depends on 1)

A composition according to claim 1 wherein the compound is of the formula ##STR18## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.4 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxyl; and R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxyl.

### Claim 4 (depends on 3)

A composition according to claim 3 wherein Y is attached to the R.sub.4 substituted phenyl ring in the 3- or 4-position.

### Claim 5 (depends on 4)

A composition according to claim 4 wherein R.sub.4 is hydrogen, fluorine or chlorine and R.sub.5 is hydrogen, fluorine or chlorine.

### Claim 6 (depends on 1)

A composition according to claim 1 wherein the compound is of the formula ##STR19## wherein X is CO or CHOH; R.sub.1 is hydrogen or methyl and R.sub.8 is hydrogen, fluorine or chlorine.

### Claim 7 (depends on 6)

A composition according to claim 6 wherein the compound is 4-benzoyl-phenyl-2-pentanone.

### Claim 8 (depends on 6)

A composition according to claim 6 in oral administration form.

### Claim 9 (depends on 2)

A method according to claim 2 wherein the compound is of the formula ##STR20## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.4 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxyl; and R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxyl.

### Claim 10 (depends on 9)

A method according to claim 9 wherein Y is attached to the R.sub.4 substituted phenyl ring in the 3- or 4-position.

### Claim 11 (depends on 10)

A method according to claim 10 wherein R.sub.4 is hydrogen, fluorine or chlorine and R.sub.5 is hydrogen, fluorine or chlorine.

### Claim 12 (depends on 2)

A method according to claim 2 wherein the compound is of the formula ##STR21## wherein X is CO or CHOH; R.sub.1 is hydrogen or methyl and R.sub.8 is hydrogen, fluorine or chlorine.

### Claim 13 (depends on 12)

A method according to claim 12 wherein the compound is 4-benzoyl-phenyl-2-pentanone.

### Claim 14 (depends on 12)

A method according to claim 12 wherein the administration is oral.