Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones

Claim 2

A compound of the formula ##STR14## where n=0, 1, or 2;

Claim 3

R 1 =C 1 -C 6 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- and polyhalo- C 1 -C 4 alkyl; R 2 and R 3 , the same or different= ##STR15## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , NH 2 , --N(CH 3 ) 2 , NO 2 , CH 3 S--, CH 3 SO 2 --, or Y 1 and Y 2 taken together forming a dioxymethylene bridge; provided, when R 1 =C 1 -C 4 alkyl, C 3 -C 4 haloalkyl with halogen substituted at the 3 or 4 position, allyl, or acetonyl, both Y 1 and Y 2 cannot be H; R 4 =C 1 -C 6 alkyl, allyl, CH 2 CH 2 N(R 5 ) 2 , ##STR16## 2-tetrahydropyranyl, 2-tetrahydrofuranyl, ##STR17## where R 5 =methyl or ethyl; R 6 =H or methyl; R 7 =C 1 -C 3 alkyl, benzyl, -CH 2 CH 2 OCH 3 ##STR18## R 8 =C 1 -C 4 alkyl or benzyl; R 9 =C 1 -C 4 alkyl or benzyl; R 10 =C 1 -C 6 alkyl; R 11 =H, methyl or ethyl; R 12 =H, methyl or ethyl; R 13 =C 1 -C 6 alkyl; R 14 =C 1 -C 6 alkyl; R 15 =C 1 -C 4 alkyl; Ar= ##STR19## where Y 3 =H, F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or nitro; provided when ##STR20## then n must be 0.

Claim 4

R 1 =C 1 -C 6 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- and polyhalo- C 1 -C 4 alkyl; R 2 and R 3 , the same or different= ##STR15## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , NH 2 , --N(CH 3 ) 2 , NO 2 , CH 3 S--, CH 3 SO 2 --, or Y 1 and Y 2 taken together forming a dioxymethylene bridge; provided, when R 1 =C 1 -C 4 alkyl, C 3 -C 4 haloalkyl with halogen substituted at the 3 or 4 position, allyl, or acetonyl, both Y 1 and Y 2 cannot be H; R 4 =C 1 -C 6 alkyl, allyl, CH 2 CH 2 N(R 5 ) 2 , ##STR16## 2-tetrahydropyranyl, 2-tetrahydrofuranyl, ##STR17## where R 5 =methyl or ethyl; R 6 =H or methyl; R 7 =C 1 -C 3 alkyl, benzyl, -CH 2 CH 2 OCH 3 ##STR18## R 8 =C 1 -C 4 alkyl or benzyl; R 9 =C 1 -C 4 alkyl or benzyl; R 10 =C 1 -C 6 alkyl; R 11 =H, methyl or ethyl; R 12 =H, methyl or ethyl; R 13 =C 1 -C 6 alkyl; R 14 =C 1 -C 6 alkyl; R 15 =C 1 -C 4 alkyl; Ar= ##STR19## where Y 3 =H, F, Cl, Br, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or nitro; provided when ##STR20## then n must be 0.

Claim 5

A compound of claim 1 where R 1 =--CF 2 CF 2 H.

Claim 6

A compound of claim 1 where R 1 =--CF 3 .

Claim 7

A compound of claim 1 where R 2 and R 3 independently, ##STR21## where Y 1 =H, Cl, or F.

Claim 8

A compound of claim 1 where R 4 =alkoxycarbonyl, alkoxymethyl, benzyloxymethyl or pivaloyloxymethyl.

Claim 9

A compound of claim 1 where n=1 or 2.

Claim 10

A compound of claim 1 where R 1 =--CF 2 CF 2 H; R 2 and R 3 , independently, ##STR22## where Y 1 =H, Cl, or F; and R 4 =alkoxycarbonyl, alkoxymethyl, benzyloxymethyl or pivaloyloxymethyl.

Claim 11

A compound of claim 1 where R 1 =CF 3 ; R 2 and R 3 , independently, ##STR23## where Y 1 =H, Cl, or F; and R 4 =alkoxycarbonyl, alkoxymethyl, benzyloxymethyl or pivaloyloxymethyl.

Claim 12

The compound of claim 1: 1-benzyloxymethyl-4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole.

Claim 13

The compound of claim 1: 4,5-diphenyl-1-ethoxycarbonyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole.

Claim 14

The compound of claim 1: 1-benzyloxymethyl-4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.

Claim 15

The compound of claim 1: 4,5-diphenyl-1-(2-tetrahydropyranyl)-2-trifluoromethylthioimidazole.

Claim 16

The compound of claim 1: 1-ethoxycarbonyl-4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylthio)imidazole.

Claim 17

The compound of claim 1: 1-ethoxycarbonyl-4(or 5)-(4-fluorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole.

Claim 18

The compound of claim 1: 4,5-bis(4-fluorophenyl)-1-(pivaloyloxymethyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.

Claim 19

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 1.

Claim 20

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 2.

Claim 21

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 3.

Claim 22

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 4.

Claim 23

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 5.

Claim 24

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 6.

Claim 25

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 7.

Claim 26

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of a compound of claim 8.

Claim 27

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 9.

Claim 28

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 10.

Claim 29

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 11.

Claim 30

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 12.

Claim 31

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 13.

Claim 32

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 14.

Claim 33

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective anti-arthritic amount of the compound of claim 15.

Claim 34

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 1.

Claim 35

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 2.

Claim 36

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 3.

Claim 37

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 4.

Claim 38

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 5.

Claim 39

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 6.

Claim 40

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 7.

Claim 41

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of a compound of claim 8.

Claim 42

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 9.

Claim 43

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 10.

Claim 44

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 11.

Claim 45

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 12.

Claim 46

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 13.

Claim 47

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 14.

Claim 48

A method of treating arthritis in a mammal in need of such treatment which comprises administering to the mammal an effective antiarthritic amount of the compound of claim 15.

Claim 49

A compound of claim 1 wherein at least one of R 2 and R 3 = ##STR24## where Y 1 =C 1 -C 4 alkoxy.

Claim 50

A compound of claim 1 wherein R 4 =--CH 2 OCH 2 ##STR25## 2-tetrahydropyranyl, 2-tetrahydrofuranyl or --SO 2 Ar.

Claim 51

A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of a compound of claim 46.

Claim 52

A method of treating pain in a mammal in need of such treatment which comprises administering to the mammal an effective analgesic amount of a compound of claim 46.

Claim 53

A compound of claim 1 where n=0, 1, or 2; R 1 =C 1 -C 4 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- and polyhalo- C 1 -C 4 alkyl; R 2 and R 3 , the same or different= ##STR26## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , NH 2 , -N(CH 3 ) 2 , NO 2 , CH 3 S-, CH 3 SO 2 -, or Y 1 and Y 2 taken together forming a dioxymethylene bridge; R 4 =C 1 -C 3 alkyl, methoxymethyl, benzyloxymethyl, methoxycarbonyl, ethoxycarbonyl, and 2-tetrahydropyranyl; provided, when R 1 =C 1 -C 4 alkyl, C 3 -C 4 haloalkyl with halogen substituted at the 3 or 4 position, allyl, or acetonyl, both Y 1 and Y 2 cannot be H.