Claims
- 1. A compound selected from the group consisting of:Methyl-4-[-2-glycyl-4-(trifluoromethylphenyl)acetyl]-3-(R,S)-[(1-pyrrolidinyl)-methyl]-1-piperazinecarboxylate; Methyl-4-[(2-[N,N-bis-methylsulf onamido]-4-trifluoromethyphenyl)acetyl]-3-(R,S )-[(1-pyrrolidinyl)-methyl]-1-piperazinecarboxylate dihydrochloride; Methyl-4-[(2-[N-methylsulfonamido]phenyl)acetyl]-3-(R,S)-[(1-pyrrolidinyl)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(2-[N,N-bis-methylsulfonamido]phenyl)acetyl]-3-(R,S)-[(1-pyrrolidinyl) methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(2-[N-methylamino)sulfamyl]phenyl)acetyl]-3-(R,S)-[(1-pyrrolidinyl) methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[-4-[N-methylamino)sulfamyl]phenyl)acetyl]-3-(R,S)-[(1-pyrrolidinyl) methyl]-1-piperazinecarboxylate hydrochloride; 4-Trifluoroacetyl-1-[(trans-3-furanacrylate]-2-(R,S)-(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Trifluoroacetyl-1-[(-4-trifluoromethylphenyl)acetyl]-2-(R,S)-(1-pyrrolidinyl) methyl]piperazine hydrochloride; Methyl-4-[(3,4-dichlorophenyl)acetyl]-3-(R,S)-[(4′-methylpiperazinecarboxylate) methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(4-α,α,α-trifluoromethylphenyl)acetyl]-3-(R,S)-[3-(S)-(4′-α,α, α-trifluoro methylphenylacetate)-1-(pyrrolidinyl)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(3,4-dichlorophenyl)acetyl]-3-(R,S)-[(2-(S)-pyrrolidinemethyl-3′,4′-dichlorophenyl acetate)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(3,4-dichlorophenyl)acetyl]-3-(R)-[(2-(S)-pyrrolidinemethanol)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(2-nitro-4-α,α,α-trifluoromethylphenyl)acetyl]-3-(R,S)-[(2-(S)-pyrrolidine methanol)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(4-methylsulphonylphenyl)acetyl]-3-(R,S)-[(2-(S)-pyrrolidinemethyl-4′-methylsulphonylphenylacetate)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(4-methylsulphonylphenyl)acetyl]-3-(R,S)-[(2-(S)-pyrrolidinemethanol) methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(2-amino-4-α,α,α-triluoromethylphenyl)acetyl]-3-(R,S)-[(2-(S)-pyrrolidine methanol)methyl]-1-piperazinecarboxylate hydrochloride; Methyl-4-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[3-(S)-(3′,4′-dichlorophenyl acetate)-1-(pyrrolidinyl)methyl]-1-piperazinecarboxylate hydrochloride; 4-Acetyl-1-[3-(N-methylsulfonamido)phenyl]acetyl-2-(R,S)-[(1-pyrrolidinyl) methy]piperazine hydrochloride; 4-Acetyl-1-[(2-acetylamidophenyl)acetyl]-2-(R,S)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-acetylamidophenyl)acetyl]-2-(R,S)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-methylsulfonyl]phenyl)acetyl]-2-(R,S)-[3-(S)-(4′-methylsulfonyl phenyl acetate)-1-(pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-α,α,α-trifluoromethylphenyl)acetyl]-2-(R,S)-[3-(S)-(4′-α,α,α-trifluoro methylphenyl acetate)-1-(pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[3-(S)-(3′,4′-dichlorophenyl acetate)-1-(pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[(2-(S)-pyrrolidinemethyl-3′,4′dichlorophenylacetate)methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-trifluoromethylphenyl)acetyl]-2-(R,S)-[2-(S)-pyrrolidinemethyl-4′-trifluoromethylphenylacetate)methyl]piperazine hydrochloride; 4-Acetyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[(2-(S)-pyrrolidinemethanol) methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-methylsulphonylphenyl)acetyl]-2-(R,S)-[(2-(S)-pyrrolidinemethyl-4′-methylsulphonylphenylacetate)methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-methylsulphonylphenyl)acetyl]-2-(R,S)-[(2-(S)-pyrrolidinemethanol) methyl]piperazine hydrochloride; 4-Acetyl-1-[(4-trifluoromethylphenyl)acetyl]-2-(R,S)-[(2-(S)-pyrrolidinemethanol) methyl]piperazine hydrochloride; 4-Formyl-1-[(2-N-methylsulfamylphenyl)acetyl]-2-(R,S)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Carbonylimidazole-1-[(3,4-dichlorophenyl)acetyl]-2-(R)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Allyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(2-pyridyl)acetyl]-2-(R,S)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Formyl-1-[(2-pyridyl)acetyl]-2-(R,S)-[(1-pyrrolidinyl)methyl]piperazine hydrochloride; Methyl-4-[(3,4-dichlorophenyl)acetyl]-3-(S)-[(2-(S)-pyrrolidinemethanol)methyl]-1-piperazinecarboxlate hydrochloride; 4-Methanesulfonyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[3-(S)-methanesulfonate-1-(pyrrolidinyl) methyl]piperazine hydrochloride; 4-Methylsulphonyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[3-(S)-(3′,4′dichloro phenyl acetate)-1-(pyrrolidinyl)methyl]piperazine hydrochloride; 4-Methylsulphonyl-1-[(3,4-dichlorophenyl)acetyl]-2-(R,S)-[(3-(S)-hydroxy-1-pyrrolidinyl) methyl]piperazine hydrochloride; 4-Methylsulphonyl-1-[(4-α,α,α-triflouromethylphenyl)acetyl]-2-(R,S)-[3-(S)-(4′-α,α,α-triflouromethylphenyl acetate)-1-(pyrrolidinyl)methyl]piperazine hydrochloride; 4-Methylsulphonyl-1-[(4-α,α,α-trillouromethylphenyl)acetyl]-2-(R,S)-[(3-(S)-hydroxy-1-pyrrolidinyl)methyl]piperazine hydrochloride; 4-Acetyl-1-[(3,4-dichlorophenyl)acetyl]-2-(S)-[(3′-(S)-hydroxy-1-pyrrolidine)methyl]-piperazine hydrochloride; 4-Acetyl-1-[(3 ,4-dichlorophenyl)acetyl]-2-(R)-[(3′-(R)-hydroxy-1-pyrrolidine)methyl]-piperazine hydrochloride; and 4-Acetyl-1-[(3,4-dichlorophenyl)acetyl]-2-(S)-[(3′-(R)-hydroxy-1-pyrrolidine)methyl]-piperazine hydrochloride.
- 2. A pharmaceutical composition comprising a compound of claim 1 in a pharmaceutically acceptable carrier.
- 3. A method of treating hyperalgesia in a patient comprising administering to said patient an effective amount of a compound of claim 1.
- 4. A method of treating hyperalgesia in a patient comprising administering to said patient an effective amount of the pharmaceutical compositoin of claim 2.
- 5. A pharmaceutical composition comprising a compound of claim 1 and an antibiotic, antiviral, antifungal, anti-inflammatory agent or a mixture thereof in a pharmaceutically acceptable carrier.
Parent Case Info
This application is a continuation-in-part of application Ser. No. 09/034,661 filed on Mar. 3, 1998, now allowed which in turn is a divisional of application Ser. No. 08/899,086 filed on Jul. 23, 1997, now U.S. Pat. No. 5,744,458, which in turn is a divisional of application Ser. No. 08/796,078, filed on Feb. 5, 1997, now U.S. Pat. No. 5,688,955, which in turn is a continuation of application Ser. No. 08/612,680, filed on Mar. 8, 1996, now U.S. Pat. No. 5,646,151.
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Continuations (1)
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Number |
Date |
Country |
Parent |
08/612680 |
Mar 1996 |
US |
Child |
08/796078 |
|
US |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
09/034661 |
Mar 1998 |
US |
Child |
09/150369 |
|
US |