Claims
- 1. A compound produced by the process comprising the process step of reacting the starting compound of the formula: with FeCl3 in the presence of acetic acid, wherein the reaction mixture is heated and the temperature of the reaction mixture is about 85° C. to about reflux temperature, and wherein R1 in the above formula represents a lower alkyl (C1-C6) substituent which may be straight or branched and R2 in the above formula represents an aryl substituent of the formula: V represents a substituent selected from the group consisting of COOR3, CONR4R5, SO2NR6R7 and W, X, Y and Z represent the same or different substituents selected from the group consisting of H, alkyl, halogen, CF3, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl COOR′ and CONR″R′″; Q and the carbon atoms to which it is attached represent a heterocyclic ring selected from the group consisting of wherein the bond between positions a, b of said heterocyclic ring forms a common bond with aromatic ring (Ar); R3 and R′ are the same or different and represent H or an alkyl (C1-C6) substituent; R4, R5, R6, R7, R″ and R′″ are the same or different and represent H, an alkyl substituent, an aryl substituent, an aralkyl substituent, a heterocyclic substituent, a heterocyclicalkyl substituent, or a carboxyalkyl substituent, said aryl substituent and the aryl moiety of said aralkyl substituent having the formula: wherein Q, V, W, X, Y and Z are as previously defined, said heterocyclic substituent or the heterocyclic moiety of said heterocyclicalkyl substituent having the formula wherein A is selected from the group consisting of carbon, nitrogen, sulfur or oxygen, and R8, R9, R10, R11 are the same or different and represent H, alkyl, halogen, CF3, alkoxy, alkylthio, OH, alkylamino, dialkylamino, COOH, CONH2 and SO2NH2, and the isomers and pharmaceutically acceptable salts of said compound.
- 2. The compound according to claim 1, wherein said reaction mixture is heated for about 12 hours.
- 3. The compound according to claim 1, wherein the reaction mixture is refluxed for 12 hours.
- 4. The compound according to claim 1, wherein the temperature is from about 85° C. to about 100° C.
- 5. The compound according to claim 1, wherein said temperature is from about 90° C. to about 100° C.
- 6. The compound according to claim 1, wherein said starting compound is 3-methyl-4-(3-acetyl-5-oxo-2-pyrazolin-1-yl)benzoic acid.
- 7. The compound according to claim 1, wherein said starting compound is 2-chloro-4-(3-acetyl-5-oxo-2-pyazolin-1-yl)benzoic acid.
- 8. The compound according to claim 1, wherein said starting compound is 4-(3-acetyl-5-oxo-2-pyrazdin-1-yl)benzene sulfonamide.
- 9. The compound according to claim 1, wherein said starting compound is 3-acetyl-1-(4-trazolyl phenyl)-4,4-dihydro-1H-pyrazol-5-one.
- 10. The compound according to claim 1, wherein said starting compound is 3-acetyl-1-(5-indazolyl phenyl)4,4-dihydro-1H-pyrazol-5-one.
- 11. The compound according to claim 1, wherein said starting compound is 3acetyl-1-(5-benzotriazolyl)-4,4-dihydro-1H-pyrazol-5-one.
Parent Case Info
The present application is a divisional of U.S. patent application Ser. No. 09/371,057, filed Aug. 9, 1999, now U.S. Pat. No. 6,180,628 which is a continuation of U.S. patent application Ser. No. 09/082,656, filed May 21, 1998, now U.S. Pat. No. 5,935,957, which is a continuation of U.S. patent application Ser. No. 08/858,649, filed May 19, 1997, now U.S. Pat. No. 5,821,243, which is a continuation-in-part of U.S. application Ser. No. 08/681,289, filed Jul. 22, 1996 (now abandoned).
US Referenced Citations (10)
Non-Patent Literature Citations (4)
Entry |
H. Fraenkel-Conrat and A. Steinschneider, “Stepwise Degradation of RNA: Periodate Followed by Aniline Cleavage,” Methods in Enzymology, 12B: 243-246 (1967). |
S.J. Plotch, M. Bouloy and R.M. Krug, “Transfer of 5′-Terminal Cap of Globin mRNA to Influenza Viral Complementary RNA during Transcription in Vitro,” Proc. Natl. Acad. Sci. USA, 76: 1618-1622 (1979). |
R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter and E. DeClerq, “Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds”, J. Virol. Methods, 20: 309-321 (1988). |
G.A. Russell and P. Bruni, “Aliphatic Semidiones—XI: Radical Anions Derived by Reduction of 1-Phenyl-3-methy-2-pyrazoline-4,5-dione, 1,2,-diphenylpyrazolidene-3,4,5-trione and 1,1′-Diphenyl-3,3′-di-methyl-4,4′-bis-2-pyrazoline-5-5′-dione (Pyrazole-blue)”, Tetrahedron, 26: 3449-3456 (1970). |
Continuations (2)
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09/082656 |
May 1998 |
US |
Child |
09/371057 |
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Parent |
08/858649 |
May 1997 |
US |
Child |
09/082656 |
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US |
Continuation in Parts (1)
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08/681289 |
Jul 1996 |
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08/858649 |
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