Intermediates in the synthesis of novel (1-phenyl-1-heterocyclyl) methanol and (1-phenyl-1-heterocyclyl)methylamine derivatives

- Astra Aktiebolag
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Claims

1. A compound of formula (6) ##STR9## wherein X is O, S or Se;

R.sub.1 is H, lower alkyl, lower alkoxy-lower alkyl, aryl-lower alkyl or CF.sub.3;
R.sub.2 is H, lower alkyl, lower alkoxy-lower alkyl, aryl-lower alkyl or CF.sub.3;
Ar is phenyl, furyl, thienyl, naphthyl, pyridyl or pyrrolyl, optionally substituted by R.sub.6; and
R.sub.6 is one or more groups selected from lower alkyl, lower acyl, halogen, lower alkoxy, CF.sub.3, OH, NO.sub.2 or NR.sub.4 R.sub.5, wherein R.sub.4 and R.sub.5 independently are H, lower alkyl or lower acyl,
with the provisos that when R.sub.1 and R.sub.2 are both hydrogen and Ar represents phenyl, then Ar is substituted by R.sub.6; and that the following five compounds are excluded:
2-methyl-5-thiazolyl phenyl ketone;
phenyl 2-phenylmethyl-4-oxazolyl ketone;
4-bromophenyl 5-thiazolyl ketone;
4-methyl-5-thiazolyl phenyl ketone; and
4-methoxyphenyl 4-methyl-5-thiazolyl ketone.
Referenced Cited
U.S. Patent Documents
5385921 January 31, 1995 Boar et al.
Other references
  • Chemical Abtracts AN 74:125538, Maier et al., Jan. 1974. Chemical Abstracts AN 69:10391, Crousier et al., Jan. 1969. Chemical Abstracts AN 1984:510794, Rahman et al., Jan. 1984. Chemical Abtracts AN 1990:515314, Imura et al., Mar. 30. Patel et al, J. Geriatric Psychiatry and Neurology, vol. 8, pp. 81-95, Apr. 1995. Chemical Abstracts AN 1987:629837, Gill et al. Dondoni et al., "Synthesis of (Trimethylsilyl)thiazoles and Reactions with Carbonyl Compounds. Selectivity Aspects and Synthetic Utility," J. Org. Chem. vol. 53, pp. 1748-1761 (1988).
Patent History
Patent number: 5849921
Type: Grant
Filed: Jun 2, 1995
Date of Patent: Dec 15, 1998
Assignee: Astra Aktiebolag (Sodertalje)
Inventors: Robin Bernad Boar (Herts), Alan John Cross (Surrey), Duncan Alastair Gray (Powys), Richard Alfred Green (Oxon)
Primary Examiner: Keith D. MacMillan
Law Firm: White & Case L.L.P.
Application Number: 8/456,637
Classifications
Current U.S. Class: 546/2714; 546/2744; 546/2747; 546/2751; The Five-membered Hetero Ring Contains Ring Selenium And Is One Of The Cyclos In A Polycyclo Ring System (548/120); Chalcogen Bonded Directly To Ring Carbon Of The Thiazole Ring (548/182); Chalcogen Attached Indirectly To The Thiazole Ring By Nonionic Bonding (548/186); The Chalcogen, X, Is In A -c(=x)- Group (548/187); Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Thiazole Ring (548/200); Plural Double Bonds Between Ring Members Of Thiazole Ring (548/202); Chalcogen Attached Indirectly To The Thiazole Ring By Nonionic Bonding (548/203); The Chalcogen, X, Is In A -c(=x)- Group (548/204); Nitrogen Attached Indirectly To The Thiazole Ring By Nonionic Bonding (548/205); 1,3-oxazoles (including Hydrogenated) (548/215); Chalcogen Bonded Directly To Ring Carbon Of The Oxazole Ring (548/225); Plural Chalcogens Bonded Directly To Ring Carbons Of The Oxazole Ring (548/226); Chalcogens Bonded Directly At 2- And 5-positions Of The Oxazole Ring (548/227); Chalcogen Bonded Directly At 5-position Of The Oxazole Ring (548/228); Chalcogen Bonded Directly At 2-position Of The Oxazole Ring (548/229); Nitrogen, Halogen, Or -c(=x)-, Wherein X Is Chalcogen, Attached Directly To The Oxazole Ring By Nonionic Bonding (548/230); 4- Or 5-position Substituent Contains Chalcogen (548/232); Cyano Or -c(=x)-, Wherein X Is Chalcogen, Attached Directly Or Indirectly To The Oxazole Ring By Nonionic Bonding (548/236); Hetero Ring Is Five-membered Having Two Or More Ring Hetero Atoms Of Which At Least One Is Nitrogen (e.g., Selenazoles, Etc.) (548/100); Plural Double Bonds Between The Ring Members Of The Oxazole Ring (548/235); 1,3-thiazoles (including Hydrogenated) (514/365); Five-membered Hetero Ring Containing At Least One Nitrogen Ring Atom (e.g., 1,2,3-triazoles, Etc.) (514/359); 1,3-oxazoles (including Hydrogenated) (514/374)
International Classification: C07D20330; C07D22730; A61K 3142; A61K 31425;