Anti-inflammatory indole derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C548S492000

Reexamination Certificate

active

06911465

ABSTRACT:
Therapeutic compounds of formula (I) wherein X is CH2or SO2; R1is an optionally substituted aryl or heteroaryl ring; R2and R3are various specified groups, R4is a group NHCOR15, NHSO2R15or OCONR16R17where R15, R16and R17are various defined groups; and R5, R6and R7are independently selected from hydrogen, a functional group or an optionally substituted hydrocarbyl groups or optionally substituted heterocyclic groups; and further provided that when R4is a group NHCOR15, R15is substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; as well as pharmaceutical compositions containing them are described and claimed. These compounds and compositions are useful in the treatment of disease mediated by MCP-1 (monocyte chemoattractant protein-1) or RANTES (Regulated Upon Activation, Normal T-cell Expressed and Secreted), such as inflammatory disease.

REFERENCES:
patent: 3557142 (1971-01-01), Bell
patent: 3776923 (1973-12-01), Remers et al.
patent: 3997557 (1976-12-01), Helsley et al.
patent: 4384994 (1983-05-01), Verber et al.
patent: 4529724 (1985-07-01), Ho
patent: 4721725 (1988-01-01), Biller et al.
patent: 4751231 (1988-06-01), Halczenko et al.
patent: 4965369 (1990-10-01), Maetzel et al.
patent: 5081145 (1992-01-01), Guindon et al.
patent: 5145845 (1992-09-01), Johnson et al.
patent: 5190968 (1993-03-01), Gillard et al.
patent: 5254563 (1993-10-01), Huth et al.
patent: 5272145 (1993-12-01), Prasit et al.
patent: 5273980 (1993-12-01), Frenette et al.
patent: 5288743 (1994-02-01), Brooks et al.
patent: 5290798 (1994-03-01), Gillard et al.
patent: 5308850 (1994-05-01), Gillard et al.
patent: 5389650 (1995-02-01), Frenette et al.
patent: 5399699 (1995-03-01), Kolasa et al.
patent: 5482960 (1996-01-01), Berryman et al.
patent: 5604253 (1997-02-01), Lau et al.
patent: 5639780 (1997-06-01), Lau et al.
patent: 5684032 (1997-11-01), Elliott et al.
patent: 5852046 (1998-12-01), Lang et al.
patent: 5877199 (1999-03-01), Birdsall et al.
patent: 5955492 (1999-09-01), Thompson et al.
patent: 6184235 (2001-02-01), Connor et al.
patent: 298 913 (1992-03-01), None
patent: 0 189 690 (1986-08-01), None
patent: 0 419 049 (1991-03-01), None
patent: 0 480 659 (1992-04-01), None
patent: 0 535 923 (1993-04-01), None
patent: 0 535 924 (1993-04-01), None
patent: 0 535 925 (1993-04-01), None
patent: 0 535 926 (1993-04-01), None
patent: 0 639 573 (1995-02-01), None
patent: 0 822 185 (1998-02-01), None
patent: 0 275 667 (1998-07-01), None
patent: 2 565 981 (1985-12-01), None
patent: 63284177 (1988-11-01), None
patent: 4273857 (1992-09-01), None
patent: WO 86 00896 (1986-02-01), None
patent: WO 92 04343 (1992-03-01), None
patent: WO 93/12780 (1993-07-01), None
patent: WO 93 16069 (1993-08-01), None
patent: WO 93/20078 (1993-10-01), None
patent: WO 94 14434 (1994-07-01), None
patent: WO 97/13615 (1997-04-01), None
patent: WO 97/30704 (1997-08-01), None
patent: WO 97/35572 (1997-10-01), None
patent: WO 98/06703 (1998-02-01), None
patent: WO 99/07351 (1999-02-01), None
patent: WO 99/07678 (1999-02-01), None
patent: WO 99/33800 (1999-07-01), None
Krutosikova, A. et al. Condensed O-, X-Heterocycles by the Transformation of Azidoncrylates.Chemical Monthly123. 807-815 (1992).
Krutosikova, A. et al. Derivatives of Furo[3.2-b]Pyrrole.Collect. Czech. Chem. Commun. 59. 473-481 (1994).
Krutosikova, A. et al. Substituted Vinyl Azides in the Synthesis of Condensed Nitrogen Heterocycles.Chem. Papers48. 268-273 (1994).
Krutosikova, A. et al. Synthesis and Reactions of Furo[3.2b]Pyrrole Type Aldehydes.Collect. Czech. Chem. Commune. 58. 2139-2149 (1993).
Krutosikova, A. et al. Synthesis and Reactions of Furo[2.3b]pyrroles. Molecules 2. 69-79 (1997).
Murakami, Y. et al. Direct Regioselective Vinylation of Indoles Using Palladium (II) Chloride.Heterocycles22. 1493-1496 (1984).
Rosenmund, P. et al. Decarboxylations of Some 1-Alkyl-2-carboxy-3-indolocetic Acids and Synthesis of a 5-Thiocyanain-2.3-dihydroindole.Chem. Ber. 108, 3538-3542 (1975).—Abstract only.
Troschutz, R. & Hoffmann, A. Synthesis of Substituted 3-Amino-4-cyano-1-oxo-1,3,5,10-tetrahy-droazepino[3.4b]indoles.J Heterocyclic Chem. 34, 1431 (1997).
Yokoyama, Y. et al. Palladium-Catalyzed Cross-Coupling Reaction: Direct Allylation of Aryl Bromides with Allyl Acetate. Tetrahedton Letters 26, 6457-6460 (1985).
Yukoyama, Y. et al. New Synthetic Method for Dehydrotryptophan Derivatives. Synthesis Studies on Indoles and Related Compounds. XXIV.Chem. Pharm. Bull. 42, 832-838 (1994).
Organic Chemistry, 5thEdition, Fessenden and Fessenden, 1994, p. 790.
Berman, J.W. et al, Localization of Monocycte Chemoattractant Peptide-l Expression in the Central Nervous System in Experimental Autoimmune Encephalomyelitis and Trauma in the Rat.J. Immunol. 156, 3017-3023 (1996).
Bobosik, V. & Krutosikova, A. Synthesis of N-Phenylsulfonyl Protected Furo[3.2-b]PyrrolesCollect. Czech. Chem. Commun. 59, 499-502 (1994).
Dandarova, M. 13C NMR Spectra of Some Substituted Furo[3.2-b]pyrroles.Magnetic Resonance Chem. 28, 830-831 (1990).
Deleuran, M. et al. Localization of monocyte chemotactic and activating facton (MCAP/MCP 1) in psoriasisJ. Dermatological Sci13, 228-236 (1996).
Grimm, M.C. et al. Enhanced expression and production of monocyte chemoattractant protein-l in inflammatory bowel disease mucosa.J. Leukocyte Biol. 59, 804-812 (Jun. 1996).
Harrison, C.-A. et al. Cyclopenta [b] indoles. Part 2. Model studies towards the tremorgenic mycotoxins.J. Chem. Soc. Perkin Trans. 1131-1136 (1995).
Hartman, G.D. & Halezenko, W. The Synthesis of 5-Alkylaminomethylthieno[2.3-b]pyrrole-5-sulfonamides.Heterocycles29, 1943-1949 (1989).
Jones, M.I., et al. Potential Role of Monocyte Chemoattractant Protein EJE in Monocyte/Macrophage-Dependent IgA Immune Complex Aveolitis in the Rat.J. Immunol149, 2147-2154 (Sep. 15, 1992).
Kataoka, K. et al. Homopiperazines as cell migration inhibitors.Chemical Abstracts. Columbus Ohio, US 123, 667 (Oct. 2, 1995).
Koch, A.E. et al. Enhanced Production of Monocyte Chemoattractant Protein-l Rheumatoid Arthritis.J. Clin. Invest. 90, 772-779 (Sep. 1992).
Korobchenko, I.V. et al. Synthesis and antiviral activity of pyrrolecarboxylic acids and derivatives.Chemical AbstractsColumbus, Ohio Access Number 119 62465 (1999).
Krutosikova, A. & Dandarova. M. Substituted Vinyl Azides in Synthesis of Furo[3.2-b.4.5-b]-Dipyrroles and Pyrrolo[213.4.5]Furo[3.2-c]Pyridines.Heterocycles37, 1695-1700 (1994).
Krutosikova. A. & Dandarova. M. Reactions of Methyl 2-Formylfuro[3.2-b]pyrrole-5-carboxylaes.Chem Papers50,72-76, (1996).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Anti-inflammatory indole derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Anti-inflammatory indole derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Anti-inflammatory indole derivatives will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3518837

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.