N-substituted piperidinyl-imidazopyridine compounds as 5-HT4...

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

C514S233200, C514S303000, C546S121000, C546S112000, C544S127000

Reexamination Certificate

active

06951867

ABSTRACT:
This invention provides a compound of the formula (I):or a pharmaceutically acceptable salt, amide or ester thereof, wherein R1represents a hydrogen atom or a halogen atom; R2represents a hydrogen atom, etc.; R3represents an alkyl group having from 1 to 10 carbon atoms; said alkyl group of R3is substituted by at least one substituent selected from the group consisting of substituents α; said substituents α is aryl, hydroxy, oxo, etc.; said aryl having 6 to 10 carbon atoms; said aryl is unsubstituted or substituted by at least one alkyl group having from 1 to 6 carbon atoms; said heterocyclic and the heterocyclic moiety of said heterocycliccarbonyl, both of substituents α, are 5- to 10-membered cyclic groups containing from 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atomsThese compounds have 5-HT4receptor binding activity, and thus are useful for the treatment of gastroesophageal reflux disease, non-ulcer dyspepsia, functional dyspepsia, irritable bowel syndrome or the like in mammalian, especially humans. This invention also provides a pharmaceutical composition comprising the above compound.

REFERENCES:
patent: 5137893 (1992-08-01), Becker et al.
patent: 5196547 (1993-03-01), Becker et al.
patent: 5219850 (1993-06-01), Becker et al.
patent: 5260303 (1993-11-01), Becker et al.
patent: 5434161 (1995-07-01), Becker et al.
patent: 5591749 (1997-01-01), Becker et al.
patent: 5604239 (1997-02-01), Becker et al.
patent: 6624162 (2003-09-01), Uchida et al.
patent: 0274867 (1988-07-01), None
patent: 0504679 (1992-09-01), None
patent: H01258674 (1989-10-01), None
patent: H02643274 (1989-10-01), None
patent: 2001006877 (2001-01-01), None
patent: WO9215593 (1992-09-01), None
patent: WO9408998 (1994-04-01), None
patent: WO9605166 (1996-02-01), None
patent: WO9727852 (1997-08-01), None
patent: WO9738665 (1997-10-01), None
patent: WO9950247 (1999-10-01), None
patent: WO0105763 (2001-01-01), None
Barnes et al. Neuropharmacology 38(1999) 1083-1085, 1118-1125.
Dumuis, et al., “A 5-HT receptor in the central nervous system, positively coupled with adenylate cyclase, is antagonized by ICS 205 930”,European Journal of Pharmacology, 146 (1988), 187-188.
Dumuis, et al., “The gastrointestinal prokinetic benzamide derivatives are agonists at the non-classical 5-HT receptor (5-HT4) positively coupled to adenylate cyclase in neurons”,Naunyn-Schmiedeberg's Arch. Pharmacol. (1989) 340: 403-410.
Bockaert, et al., “The 5-HT4 receptor: a place in the sun”,TiPs, 1992, 13, 141-145.
Ford, A.P.D.W., et al., “The 5-HT4Receptor”,Med. Res. Rev., 1993, 13, 633-662.
Gullikson, G.W., et al., “Gastrointestinal Motility Responses to the S and R Enantiomers of Zacopride, a 5-HT4 Agonist and 5-HT3 Antagonist”,Drug Dev. Res., 1992, 26, 405-417.
Eglen, et al., “Central 5-HT4 receptors”,TiPs, 1995, 16, 391-398.
Bockaert, Jr., et al., “5-HT4Receptors Potential Therapeutic Implications in Neurology and Psychiatry”,CNS Drugs, 1, 6-14 (1994).
Romanelli, M.N., et al., “Synthesis and Biological Activity of a Series of Aryl Tropanyl Esters and Amides Chemically Related to 1H-Indole-3-carboxylic Acid endo 8-Methyl-8-azabicyclo[3.2.1]oct-3-yl Ester”Arzneimittel Forschung Drug Research, 1993, 43(II), 913-918.
Kaumann, A., et al., ., “A 5-HT4-like receptor in human right atrium”,Naunyn-Schmiedeberg's Arc., Pharmacol. (1991), 344, 150-159.
Finlayson, K., et al., “[3H]Dofetilide binding to HERG transfected membranes: a potential high throughput preclinical screen”,European Journal of Pharmacology, 430, (2001), 147-148.
Mutterer, et al., “Hatogenierte Pyridine V. Fluorierte und bromierte Pyridinverbindugen”,Helv. Chim. Acta, (1976), 59, 229-235.
Barlow, et al., “Diels-Alder reactions of trochloro-1,2,4-triazine: intramolecular additions with 1,5 and 1,6 dienes”,J. Chem. Soc., Perkin Trans. I, (1996), 519-524.
Lantos, et al., “Novel Cage Compounds from Inter-intra-molecular Diels-Alder Reactions of 1,2,4-Triazines with Cyclo-octa-1,5-diene”,J. Chem. Soc., Chem. Commun. (1998), 1482-1483.
Feibush, et al., “Chiral Separation of Heterocyclic Drugs by HPLC: Solute-Stationary Phase Base-Pair Interactions”,J. Am. Chem. Soc., (1986), 108(12), 3310-3318.
G.S. Baxter, et al., “5-Hydroxytryptamine4receptors mediate relaxation of the rat oesophageal tunica muscularis mucosae”,Naunyn-Schmiedeberg's Arch. Pharmacol., (1991), 343, 439-446.
Yukiko Mine, et al, “Comparison of Effect of Mosapride Citrate and Existing 5-HT4Receptor Agonists on Gastrointestinal Motility In Vivo and In Vitro”,JPET, (1997) 283: 1000-1008.
Reeves, J.J., et al., “Investigation into the 5-hydroxytryptamine receptor mediating smooth muscle relaxation in the rat oesophagus”,British Journal of Pharmacology, (1991) 103: 1067-1072.
Z. Zhou, et al., “Properties of HERG Channels Stably Expressed in HEK 293 Cells Studied at Physiological Temperature”,Biophysical Journal, 74, 230-241.
M.C. Coldwell, et al., “The Synthesis and Dopamine D2and Serotonin 5-HT3Receptor Affinity of 3-Aza Analogues (Pyridyl) of 4-Amino-5-chloro-2-methoxybenzamides”,Biorg. Med. Chem. Lett., vol. 5, No. 1, 39-42 (1995).
D. Subhas Bose, et al., “Boron Trifluoride Promated Cleavage of Benzyl Carbamates”,Tetrahedron Lett., vol. 31, No. 47, 6903-6906, 1990.
Prugh, et al., A Simple Method of Protecting a Secondary Amine with tert Butyloxycarbonyl (BOC) in the Presence of a Primary Amine,Synth. Commun., 1992, 22, 2357-60.
G. Bertram, et al., “Total Synthesis of (±)-Strobilurin E”,Tetrahedron Lett., vol. 37, No. 44, 7955-7958, 1996.
W.C. Lumma, Jr., et al., “Condensation of Unsymmetrical Aliphatic Ketones with Formaldehyde in Trilluoroacetic Acid”,J. Org. Chem., vol. 35, No. 7, 1970, 2391-2393.
A. Otha, et al., “Stereoselective Synthesis of Spicy Components in Peppers”,Heterocycles, 1991, vol. 32, 965-73.
B.G. Hazra, et al., “An Improved Procedure for the Dichloroacetylation of Primary and Secondary Amines”,Org. Prep. Proced. Int., 1989, 21, 355-358.
G. Mattalia, et al., “Synthesis of New Derivatives of the 4,5-Diphenyloxazole Series”,Il Farmaco, Ed. Sci., 1976, 31, 457-67.
Lopez-Rodriguez, et al., “Benzimidazole Derivatives. Part 1: Synthesis and Structure-Activity Relationships of New Benzimi9dazole-4-carboxamides and Carboxylates as Potent and Selective 5-HT4 Receptor Antagonists”,Bioorganic&Medicinal Chemistry, 7 (1999), 2271-2281.
Katz, J., et al., “Action des isopropyl-9 et tertiobutyl-9 bora-9 bicyclo (3.3.1)nonanes sur quelques cétones α-bromées. Synthése de cétones substituées”,Bull. Soc. Chim. Fr., 1997,683-687.
Chem. Abstr., 1963, 58, 5570f.

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

N-substituted piperidinyl-imidazopyridine compounds as 5-HT4... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with N-substituted piperidinyl-imidazopyridine compounds as 5-HT4..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-substituted piperidinyl-imidazopyridine compounds as 5-HT4... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3478045

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