Patent US4190666A successfully refreshed from Google Patents.
US4190666A
Expired / Lapsed
US
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Anti-inflammatory 4,5-diarly-2-(substituted-thio)imidazoles and their corresponding sulfoxides and sulfones
Assignee: EIDP Inc
•
Filing: 1978-02-10
•
Granted: 1980-02-26
•
Expires: 1998-02-10
Abstract
Abstract Anti-inflammatory 4,5-diaryl-2-(substituted-thio)imidazols and their corresponding sulfoxides and sulfones useful for treating arthritis and related diseases.
Inventors
- 👤 Saul C. Cherkofsky
- 👤 Thomas R. Sharpe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:58
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/84
Claims Analysis
Total Claims: 85
Claim 1
Independent Claim
208 words
A compound of the formula ##STR16## where n=0, 1, or 2; R 1 =C 1 --C 8 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono-- or polyhalo-- C 1 -C 8 alkyl; R 2 and R 3 , the same or different= ##STR17## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , 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 n=0, 1 or 2 and Y 1 and Y 2 both=hydrogen, R 1 cannot be vinyl; provided, when R 1 =C 1 -C 8 alkyl, C 3 -C 8 haloalkyl with halogen substituted at the 3 through 8 position, allyl or --CH 2 COCH 3 , both Y 1 and Y 2 cannot be H; provided further, when n=O and R 1 =CH 3 , both Y 1 and Y 2 cannot be p-Cl or p-OCH 3 ; its pharmaceutically suitable acid addition salt where N=O or its pharmaceutically suitable metal salt where n=1 or 2.
Claim 2
Dependent Claim
208 words
A compound of the formula ##STR16## where n=0, 1, or 2; R 1 =C 1 --C 8 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono-- or polyhalo-- C 1 -C 8 alkyl; R 2 and R 3 , the same or different= ##STR17## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , 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 n=0, 1 or 2 and Y 1 and Y 2 both=hydrogen, R 1 cannot be vinyl; provided, when R 1 =C 1 -C 8 alkyl, C 3 -C 8 haloalkyl with halogen substituted at the 3 through 8 position, allyl or --CH 2 COCH 3 , both Y 1 and Y 2 cannot be H; provided further, when n=O and R 1 =CH 3 , both Y 1 and Y 2 cannot be p-Cl or p-OCH 3 ; its pharmaceutically suitable acid addition salt where N=O or its pharmaceutically suitable metal salt where n=1 or 2.
Claim 3
Dependent Claim
199 words
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-- or polyhalo-- C 1 -C 4 alkyl; R 2 and R 3 , the same or different= ##STR18## Y 1 and Y 2 , the same or different= hydrogen, C 1 -C 4 alkoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --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 n=0, 1 or 2 and Y 1 and Y 2 both=hydrogen, R 1 cannot be vinyl 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 --CH 2 COCH 3 , both Y 1 and Y 2 cannot be H; provided further, when n=o and R 1 =CH 3 , both Y 1 and Y 2 cannot be p-Cl or p-OCH 3 ; or its pharmaceutically suitable salt where n=1 or 2.
Claim 4
Dependent Claim
157 words
The compound of claim 1 where: n=0, 1, or 2; R 1 =C 1 -C 4 alkyl; allyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono-- and polyfluoro C 1 -C 4 alkyl; R 2 and R 3 , the same or different= ##STR19## Y 1 and Y 2 , the same or different=hydrogen, methoxy, ethoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --N(CH 3 ) 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 fluoroalkyl with the fluorine substituted at the 3 or 4 position, allyl, or --CH 2 COCH 3 , both Y 1 and Y 2 cannot be H; provided further, when n=0 and R 1 =CH 3 , both Y 1 and Y 2 cannot be p-Cl or p-OCH 3 .
Claim 5
Dependent Claim
13 words
The compound of claim 1 where R 1 =--CF 2 CF 2 H.
Claim 6
Dependent Claim
11 words
The compound of claim 1 where R 1 =--CF 3 .
Claim 7
Dependent Claim
20 words
The compound of claim 1 where R 2 and R 3 independently,= ##STR20## where Y 1 =H, Cl, or F.
Claim 8
Dependent Claim
9 words
The compound of claim 1 where n=1 or 2.
Claim 9
Dependent Claim
34 words
The compound of claim 3 where R 1 =--CF 2 CF 2 H; R 2 and R 3 , independently, = ##STR21## where Y 1 =H, Cl, or F; and n=0, 1, or 2.
Claim 10
Dependent Claim
31 words
The compound of claim 3 where R 1 =--CF 3 ; R 2 and R 3 , independently, = ##STR22## Y 1 =H, Cl, or F; an n=0, 1, or 2.
Claim 11
Dependent Claim
33 words
The compound of claim 3 where R 1 =--CF 2 CF 2 H; R 2 and R 3 , independently, = ##STR23## where Y 1 =H, Cl, or F; and n=0 or 2.
Claim 12
Dependent Claim
8 words
The compound of claim 3: 4(or 5)-(3,4-dichlorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 13
Dependent Claim
6 words
The compound of claim 3: 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 14
Dependent Claim
8 words
The compound of claim 3: 4(or 5)-(4-fluorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 15
Dependent Claim
6 words
The compound of claim 3: 4,5-bis(4-chlorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 16
Dependent Claim
8 words
The compound of claim 3: 4(or 5)-(4-chlorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 17
Dependent Claim
6 words
The compound of claim 3: 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 18
Dependent Claim
6 words
The compound of claim 3: 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole.
Claim 19
Dependent Claim
6 words
The compound of claim 3: 4,5-diphenyl-2-trifluoromethylsulfonylimidazole.
Claim 20
Dependent Claim
6 words
The compound of claim 3: 4,5-bis(p-fluorophenyl)-2-trifluoromethylthioimidazole.
Claim 21
Dependent Claim
6 words
The compound of claim 3: 4,5-bis(p-fluorophenyl)-2-trifluoromethylsulfonylimidazole.
Claim 22
Dependent Claim
47 words
The compound of claim 3 of the formula ##STR24## where R 1 =C 1 -C 4 alkyl, monohalo- or polyhalo-C 1 -C 4 alkyl; Y 1 and Y 2 , the same or different, =H, 2-methoxy, 4-methoxy, 2-ethoxy, 4-ethoxy, 2-chloro, or 4-chloro; and n=0, 1, or 2.
Claim 23
Dependent Claim
49 words
The compound of claim 21 where R 1 =polyhalo-C 1 -C 2 alkyl; Y 1 and Y 2 , the same or different=H, 2-methoxy, 4-methoxy, 2-ethoxy, 4-ethoxy, 2-chloro, or 4-chloro; provided, that at least one of Y 1 and Y 2 =4-methoxy or 4-ethoxy; and n=0, 1 or 2.
Claim 24
Dependent Claim
6 words
The compound of claim 22: 4,5-bis(4-methoxyphenyl)-2-(1,1,2-trifluoroethylsulfonyl)imidazole.
Claim 25
Dependent Claim
6 words
The compound of claim 22: 4,5-bis(4-methoxyphenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 26
Dependent Claim
6 words
The compound of claim 22: 4,5-bis(4-methoxyphenyl)-2-(2,2,2-trifluoroethylthio)imidazole.
Claim 27
Dependent Claim
6 words
The compound of claim 22: 4,5-bis(4-methoxyphenyl)-2-(2,2,2-trifluoroethylsulfinyl)imidazole.
Claim 28
Dependent Claim
6 words
The compound of claim 22: 4,5-bis(4-methoxyphenyl)-2-(2,2,2-trifluoroethylsulfonyl)imidazole.
Claim 29
Dependent Claim
6 words
The compound of claim 22: 4,5-bis(4-methoxyphenyl)-2-(trifluoromethylsulfonyl)imidazole.
Claim 30
Dependent Claim
182 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of a compound of the formula ##STR25## where n=0, 1, or 2; R 1 =C 1 -C 8 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- or polyhalo- C 1 -C 8 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, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --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 8 alkyl, C 3 -C 4 haloalkyl with the halogen substituted at the 3 through 8 position, allyl, or --CH 2 COCH 3 both Y 1 and Y 2 cannot be H; its pharmaceutically suitable acid addition salt where n=0 or its pharmaceutically suitable metal salt where n=1 or 2.
Claim 31
Dependent Claim
182 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective antiarthritic amount of a compound of the formula ##STR25## where n=0, 1, or 2; R 1 =C 1 -C 8 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- or polyhalo- C 1 -C 8 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, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --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 8 alkyl, C 3 -C 4 haloalkyl with the halogen substituted at the 3 through 8 position, allyl, or --CH 2 COCH 3 both Y 1 and Y 2 cannot be H; its pharmaceutically suitable acid addition salt where n=0 or its pharmaceutically suitable metal salt where n=1 or 2.
Claim 32
Dependent Claim
134 words
The compound of claim 29 where n=0, 1, or 2; R 1 =C 1 -C 4 alkyl; allyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- or polyfluoro- C 1 -C 4 alkyl; R 2 and R 3 , the same or different = ##STR27## Y 1 and Y 2 , the same or different=hydrogen, methoxy, ethoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --N(CH 3 ) 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 fluoroalkyl with the fluorine substituted at the 3 or 4 position, allyl, or --CH 2 COCH 3 both Y 1 and Y 2 cannot be H.
Claim 33
Dependent Claim
13 words
The compound of claim 29 wherein R 1 =--CF 2 CF 2 H.
Claim 34
Dependent Claim
11 words
The compound of claim 29 where R 1 =--CF 3 .
Claim 35
Dependent Claim
20 words
The composition of claim 29 where R 2 and R 3 independently= ##STR28## where Y 1 =H, Cl, or F.
Claim 36
Dependent Claim
9 words
The compound of claim 29 where n=1 or 2.
Claim 37
Dependent Claim
34 words
The composition of claim 30 where R 1 =--CF 2 CF 2 H; R 2 and R 3 , independently, = ##STR29## where Y 1 =H, Cl, or F; and n=0, 1, or 2.
Claim 38
Dependent Claim
32 words
The composition of claim 30 where R 1 =--CF 3 ; R 2 and R 3 , independently, = ##STR30## where Y 1 =H, Cl, or F; and n=0, 1, or 2.
Claim 39
Dependent Claim
33 words
The composition of claim 30 where R 1 =--CF 2 CF 2 H: R 2 and R 3 , independently, = ##STR31## where Y 1 =H, Cl, or F; and n=0 or 2.
Claim 40
Dependent Claim
12 words
The composition of claim 29 where the compound is 4(or 5)-(3,4-dichlorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 41
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 42
Dependent Claim
12 words
The composition of claim 30 where the compound is 4(or 5)-4-fluorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 43
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-bis(4-chlorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 44
Dependent Claim
12 words
The composition of claim 30 where the compound is 4(or 5)-(4-chlorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 45
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 46
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole.
Claim 47
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-diphenyl-2-trifluoromethylsulfonylimidazole.
Claim 48
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-bis(p-fluorophenyl)-2-trifluoromethylthioimidazole.
Claim 49
Dependent Claim
10 words
The composition of claim 30 where the compound is 4,5-bis(p-fluorophenyl)-2-trifluoromethylsulfonylimidazole.
Claim 50
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 21.
Claim 51
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 22.
Claim 52
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 23.
Claim 53
Dependent Claim
19 words
A phamaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 24.
Claim 54
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 25.
Claim 55
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 26.
Claim 56
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharamceutical carrier and an effective analgesic amount of the compound of claim 27.
Claim 57
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective analgesic amount of the compound of claim 28.
Claim 58
Independent Claim
187 words
A method of treating arthritis in a mammal which comprises administering to the mammal an effective anti-arthritic amount of a compound of the formula ##STR32## where n=0, 1, or 2; R 1 =C 1 -C 8 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- or polyhalo- C 1 -C 8 alkyl; R 2 and R 3 , the same or different = ##STR33## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --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 8 alkyl, C 3 -C 4 haloalkyl with the halogen substituted at the 3 through 8 position, allyl, or --CH 2 COCH 3 both Y 1 and Y 2 cannot be H; its pharmaceutically suitable acid addition salt where n=0 or its pharmaceutically suitable metal salt where n=1 or 2.
Claim 59
Independent Claim
187 words
A method of treating arthritis in a mammal which comprises administering to the mammal an effective anti-arthritic amount of a compound of the formula ##STR32## where n=0, 1, or 2; R 1 =C 1 -C 8 alkyl; allyl; vinyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- or polyhalo- C 1 -C 8 alkyl; R 2 and R 3 , the same or different = ##STR33## Y 1 and Y 2 , the same or different=hydrogen, C 1 -C 4 alkoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --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 8 alkyl, C 3 -C 4 haloalkyl with the halogen substituted at the 3 through 8 position, allyl, or --CH 2 COCH 3 both Y 1 and Y 2 cannot be H; its pharmaceutically suitable acid addition salt where n=0 or its pharmaceutically suitable metal salt where n=1 or 2.
Claim 60
Dependent Claim
135 words
The method of claim 56 where n=0, 1, or 2; R 1 =C 1 -C 4 alkyl; allyl; --CH 2 COCH 3 ; --CH 2 S(O) m CH 3 , where m=0, 1, or 2; mono- or polyfluoro- C 1 -C 4 alkyl; R 2 and R 3 , the same or different = ##STR34## Y 1 and Y 2 , the same or different=hydrogen, methoxy, ethoxy, acetoxy, C 1 -C 4 alkyl, Cl, F, CF 3 , --N(CH 3 ) 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 fluoroalkyl with the fluorine substituted at the 3 or 4 position, allyl, or --CH 2 COCH 3 , both Y 1 and Y 2 cannot be H.
Claim 61
Dependent Claim
13 words
The method of claim 56 where R 1 =--CF 2 CF 2 H.
Claim 62
Dependent Claim
11 words
The method of claim 56 where R 1 =--CF 3 .
Claim 63
Dependent Claim
21 words
The method of claim 56 where R 2 and R 3 independently = ##STR35## where Y 1 =H, Cl, or F.
Claim 64
Dependent Claim
9 words
The method of claim 56 where n=1 or 2.
Claim 65
Dependent Claim
34 words
The method of claim 57 where R 1 =--CF 2 CF 2 H; R 2 and R 3 , independently, = ##STR36## where Y 1 =H, Cl, or F.; and n=0, 1 or 2.
Claim 66
Dependent Claim
33 words
The method of claim 57 where R 1 =--CF 2 CF 2 H; R 2 and R 3 , independently, = ##STR37## where Y 1 =H, Cl, or F.; and n=0 or 2.
Claim 67
Dependent Claim
32 words
The method of claim 57 where R 1 =--CF 3 ; R 2 and R 3 , independently, = ##STR38## where Y 1 =H, Cl, or F.; and n=0, 1 or 2.
Claim 68
Dependent Claim
12 words
Th method of claim 56 where the compound is 4(or 5)-(3,4-dichlorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 69
Dependent Claim
10 words
The method of claim 57 where the compound is 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 70
Dependent Claim
12 words
The method of claim 57 where the compound is 4(or 5)-(4-fluorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 71
Dependent Claim
10 words
The method of claim 57 where the compound is 4,5-bis(4-chlorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 72
Dependent Claim
12 words
The method of claim 57 where the compound is 4(or 5)-(4-chlorophenyl)-5(or 4)-phenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 73
Dependent Claim
10 words
The method of claim 57 where the compound is 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole.
Claim 74
Dependent Claim
10 words
The method of claim 57 where the compound is 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylthio)imidazole.
Claim 75
Dependent Claim
10 words
The compound of claim 57 where the compound is 4,5-diphenyl-2-trifluoromethylsulfonylimidazole.
Claim 76
Dependent Claim
10 words
The method of claim 57 where the compound is 4,5-bis(p-fluorophenyl)-2-trifluoromethylthioimidazole.
Claim 77
Dependent Claim
10 words
The method of claim 57 where the compound is 4,5-bis(p-fluorophenyl)-2-trifluoromethylsulfonylimidazole.
Claim 78
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of a compound of claim 21.
Claim 79
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of a compound of claim 22.
Claim 80
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of the compound of claim 23.
Claim 81
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of the compound of claim 24.
Claim 82
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal and ffective analgesic amount of the compound of claim 25.
Claim 83
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of the compound of claim 26.
Claim 84
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of the compound of claim 27.
Claim 85
Dependent Claim
24 words
A method of alleviating pain in a mammal which comprises administering to the mammal an effective analgesic amount of the compound of claim 28.
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) | 1983-02-25 | 1983-08-27 | 1984-02-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-25 | 1987-08-27 | 1988-02-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-25 | 1991-08-27 | 1992-02-26 | $7700.00 | Window Closed / Lapsed |