Title:
IMIDAZOLE DERIVATIVES AND THE USE THEREOF AS NITROGEN MONOXIDE SYNTHASE INHIBITORS
Document Type and Number:
WIPO Patent Application WO1997015555
Kind Code:
A3
Abstract:
The invention relates to the compounds of the formula (I), and to the preparation and use thereof in drugs.
Inventors:
HOELSCHER PETER (DE)
REHWINKEL HARTMUT (DE)
BURTON GERARDINE (DE)
PHILLIPS GARY (DE)
PARKINSON JOHN (DE)
REHWINKEL HARTMUT (DE)
BURTON GERARDINE (DE)
PHILLIPS GARY (DE)
PARKINSON JOHN (DE)
Application Number:
PCT/DE1996/002079
Publication Date:
July 10, 1997
Filing Date:
October 24, 1996
Export Citation:
Assignee:
SCHERING AG (DE)
HOELSCHER PETER (DE)
REHWINKEL HARTMUT (DE)
BURTON GERARDINE (DE)
PHILLIPS GARY (DE)
PARKINSON JOHN (DE)
HOELSCHER PETER (DE)
REHWINKEL HARTMUT (DE)
BURTON GERARDINE (DE)
PHILLIPS GARY (DE)
PARKINSON JOHN (DE)
International Classes:
A61K31/00; A61K31/415; A61K31/4164; A61K31/4178; A61K31/44; A61K31/4427; A61K31/443; A61K31/4433; A61K31/4439; A61P43/00; C07D233/56; C07D233/60; C07D233/68; C07D233/70; C07D233/84; C07D401/04; C07D403/10; C07D405/04; C07D405/12; C07D409/10; C07D409/14; C07D521/00; (IPC1-7): C07D/
Foreign References:
| EP0385850A2 | 1990-09-05 | |||
| DE3942475A1 | 1991-06-27 | |||
| FR2267101A1 | 1975-11-07 | |||
| EP0270091A1 | 1988-06-08 | |||
| US3541109A | 1970-11-17 |
Other References:
J. OHMORI ET. AL.: "6-(1H-Imidazol-1-yl)-7-nitro-2,3-(1H,4H) quinoxazolinedione Hydrochloride (YM90K) and Related Compounds. Structure-activity Relationships for the AMPA-Type Non-NMDA Receptor.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 4, 18 February 1994 (1994-02-18), WASHINGTON DC, US, pages 467 - 75, XP002029804
D. M. ZIMMERMANN ET. AL.: "Structure-activity Relationships of trans-3,4-Dimethyl-4-(3-hydroxyphenyl)-piperidine Antagonists for mu and kappa-Opioid Receptors.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 36, no. 20, 1 October 1993 (1993-10-01), WASHINGTON DC, US, pages 2964 - 72, XP002029805
C. ESCOLASTICO ET. AL.: "Imidazole and Benzimidazole Addition to Quinones. Formation of meso and d,l Isomers and Crystal Structure of the d,l Isomer of 2,3-Bis(benzimidazol-1'-yl)- 1,4-Dihydroxybenzene.", TETRAHEDRON, vol. 50, no. 43, 1994, OXFORD, GB, pages 12489 - 12510, XP000652111
J. W. LAMPE ET. AL.: "A Novel Rearangement of 1-(2-Aminoaryl)imidazoles.", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 31, no. 2, March 1994 (1994-03-01), pages 287 - 91, XP000653292
P. FRANCHETTI ET. AL.: "Structure-Activity Relationships in Reactions of Organophosphorus Inhibited Acetylcholinesterase. 7. 1-Aryl-2-hydroxyiminomethyl-3-methylimidazolium Iodides.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 17, no. 1, January 1974 (1974-01-01), WASHINGTON DC, US, pages 18 - 22, XP000653251
A. L. JOHNSON ET. AL.: "The Synthesis of 1-Arylimidazoles, a New Class of Steroid Hydroxylation Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, vol. 12, no. 6, November 1969 (1969-11-01), WASHINGTON DC, US, pages 1024 - 8, XP000653294
E. L. PLUMMER ET. AL.: "Heterocyclic Analogues of Substituted (1,1'-Biphenyl)-3-methyl pyrethroid Insecticides.", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 32, no. 5, September 1984 (1984-09-01), WASHINGTON DC, US, pages 1116 - 21, XP000653215
J. F. K. WILSHIRE: "The Preparation of 4-Fluoro-3-nitrobenzonitrile and the Proton Magnetic Resonance Spectra of some Compounds Containing the N-4-Cyano-2-nitrophenyl Group.", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 20, no. 10, October 1967 (1967-10-01), MELBOURNE, AU, pages 2269 - 73, XP000653235
J. F. K. WILSHIRE: "The Preparation of 2-Fluoro-5-nitrobenzonitrile and the Proton Magnetic Resonance Spectra of some Compounds Containing the N-(2-Cyano-4-nitrophenyl) Group.", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 20, no. 10, October 1967 (1967-10-01), MELBOURNE, AU, pages 1663 - 70, XP000653236
R. G. R. BACON ET. AL.: "Metal Ions and Complexes in Organic Reactions. Part XVIII.", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS I, no. 16, 1974, OXFORD, GB, pages 1970 - 5, XP000653267
P. STREHLKE: "Antifungale Imidazolverbindungen II. Äther von (1-Imidazolyl)- phenolen.", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, CHIMICA THERAPEUTICA, vol. 14, no. 3, May 1979 (1979-05-01), pages 227 - 30, XP000653317
D. POORANCHAND ET. AL.: "Reaction of Dimethyl N-aryl and N-alkylcarbonimidodithioates with Aminoacetaldehyde Diethyl Acetal. A Direct Synthesis of 1-Aryl and 1-Alkyl-2-methylthioimidazoles.", SYNTHESIS, no. 12, December 1987 (1987-12-01), STUTTGART, DE, pages 1136 - 8, XP002029808
D. J. WOLFFE ET. AL.: "Calmodulin-dependent Nitric-oxide Synthase", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 268, no. 13, 5 May 1993 (1993-05-05), ROCKVILLE PIKE, US, pages 9425 - 9, XP000652112
CHEMICAL ABSTRACTS, vol. 125, no. 21, 18 November 1996, Columbus, Ohio, US; abstract no. 265016r, R. L. HANDY ET. AL.: "Inhibition of nitric oxide synthase by 1-(2-trifluoromethylphenyl) imidazole." page 38; column 1; XP002029806
D. M. ZIMMERMANN ET. AL.: "Structure-activity Relationships of trans-3,4-Dimethyl-4-(3-hydroxyphenyl)-piperidine Antagonists for mu and kappa-Opioid Receptors.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 36, no. 20, 1 October 1993 (1993-10-01), WASHINGTON DC, US, pages 2964 - 72, XP002029805
C. ESCOLASTICO ET. AL.: "Imidazole and Benzimidazole Addition to Quinones. Formation of meso and d,l Isomers and Crystal Structure of the d,l Isomer of 2,3-Bis(benzimidazol-1'-yl)- 1,4-Dihydroxybenzene.", TETRAHEDRON, vol. 50, no. 43, 1994, OXFORD, GB, pages 12489 - 12510, XP000652111
J. W. LAMPE ET. AL.: "A Novel Rearangement of 1-(2-Aminoaryl)imidazoles.", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 31, no. 2, March 1994 (1994-03-01), pages 287 - 91, XP000653292
P. FRANCHETTI ET. AL.: "Structure-Activity Relationships in Reactions of Organophosphorus Inhibited Acetylcholinesterase. 7. 1-Aryl-2-hydroxyiminomethyl-3-methylimidazolium Iodides.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 17, no. 1, January 1974 (1974-01-01), WASHINGTON DC, US, pages 18 - 22, XP000653251
A. L. JOHNSON ET. AL.: "The Synthesis of 1-Arylimidazoles, a New Class of Steroid Hydroxylation Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, vol. 12, no. 6, November 1969 (1969-11-01), WASHINGTON DC, US, pages 1024 - 8, XP000653294
E. L. PLUMMER ET. AL.: "Heterocyclic Analogues of Substituted (1,1'-Biphenyl)-3-methyl pyrethroid Insecticides.", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 32, no. 5, September 1984 (1984-09-01), WASHINGTON DC, US, pages 1116 - 21, XP000653215
J. F. K. WILSHIRE: "The Preparation of 4-Fluoro-3-nitrobenzonitrile and the Proton Magnetic Resonance Spectra of some Compounds Containing the N-4-Cyano-2-nitrophenyl Group.", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 20, no. 10, October 1967 (1967-10-01), MELBOURNE, AU, pages 2269 - 73, XP000653235
J. F. K. WILSHIRE: "The Preparation of 2-Fluoro-5-nitrobenzonitrile and the Proton Magnetic Resonance Spectra of some Compounds Containing the N-(2-Cyano-4-nitrophenyl) Group.", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 20, no. 10, October 1967 (1967-10-01), MELBOURNE, AU, pages 1663 - 70, XP000653236
R. G. R. BACON ET. AL.: "Metal Ions and Complexes in Organic Reactions. Part XVIII.", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS I, no. 16, 1974, OXFORD, GB, pages 1970 - 5, XP000653267
P. STREHLKE: "Antifungale Imidazolverbindungen II. Äther von (1-Imidazolyl)- phenolen.", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, CHIMICA THERAPEUTICA, vol. 14, no. 3, May 1979 (1979-05-01), pages 227 - 30, XP000653317
D. POORANCHAND ET. AL.: "Reaction of Dimethyl N-aryl and N-alkylcarbonimidodithioates with Aminoacetaldehyde Diethyl Acetal. A Direct Synthesis of 1-Aryl and 1-Alkyl-2-methylthioimidazoles.", SYNTHESIS, no. 12, December 1987 (1987-12-01), STUTTGART, DE, pages 1136 - 8, XP002029808
D. J. WOLFFE ET. AL.: "Calmodulin-dependent Nitric-oxide Synthase", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 268, no. 13, 5 May 1993 (1993-05-05), ROCKVILLE PIKE, US, pages 9425 - 9, XP000652112
CHEMICAL ABSTRACTS, vol. 125, no. 21, 18 November 1996, Columbus, Ohio, US; abstract no. 265016r, R. L. HANDY ET. AL.: "Inhibition of nitric oxide synthase by 1-(2-trifluoromethylphenyl) imidazole." page 38; column 1; XP002029806
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