Abstract: A process for preparing a substantially pure enantiomer of a compound formula (I) ##STR1## wherein X is O or S; andR.sup.2 represents hydrogen, --CF.sub.3, --OR.sup.7, --SR.sup.7, --NR.sup.7 R.sup.8, --CN, --COOR.sup.7, --CONR.sup.7 R.sup.8, or a saturated or unsaturated, substituted or unsubstituted hydrocarbon group, wherein R.sup.7 and R.sup.8 are independently selected from hydrogen and C.sub.1-2 alkyl provided that --NR.sup.7 R.sup.8 is other than NH.sub.2 ;which process comprises cyclization of a compound of formula (10) or salt thereof: ##STR2## wherein X and R.sup.2 are as defined in formula (I); and R.sup.4 is a labile leaving group and optionally epimerizing the endo-diastereomer so prepared to produce the corresponding exo-diastereomer.
Abstract: The compound (3R, 4R)-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1-azabicyclo[2.2.1]heptane and its salts behave as a functionally selective muscarinic agonist and are useful in the treatment of neurological and mental disorders, preferably in a pharmaceutical formulation comprising the active compound in association with a pharmaceutically acceptable carrier. The compound can be prepared by methods analogous to those known in the art via suitable chiral intermediates and cyclopropyl carboxamide oxime.
Abstract: A process for preparing substantially pure enantiomers of formula (I) ##STR1## where the * represents a chiral center, x is 0 or 1, in exo-, endo- or a mixture of exo- and endo- forms; and R is hydrogen, alkyl or aralkyl, via diastereomers of formula (IIA) or (IIB); ##STR2##
Abstract: This invention provides the 4-mono-anion of myo-inositol orthoformate, and describes a process for preparing this anion as well as the use of this anion in the preparation of a variety of mono- and poly-phosphate derivatives of myo-inositol.
Abstract: The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted circle represents one or two double bonds in any position in the 5-membered ring;X, Y and Z independently represent oxygen, sulphur, nitrogen or carbon, provided that at least one of X, Y and Z represents oxygen, sulphur or nitrogen;A represents a group of formula II: ##STR2## in which: R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, hydroxy(C.sub.1-6)alkyl, halogen, amino, cyano, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl;R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarobnyl;V represents nitrogen, ##STR3## W represents oxygen, sulphur or ##STR4## in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.
Type:
Grant
Filed:
July 13, 1990
Date of Patent:
August 20, 1991
Assignee:
Merck Sharp & Dohme Ltd.
Inventors:
Raymond Baker, John Saunders, Christopher Swain
Abstract: The present invention provides a compound of formula (I): ##STR1## or a pharmaceutically acceptable salt thereof, wherein one of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represents a hydrocarbon or hydrocarbyloxycarbonyl group and the remaining groups R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen, hydrocarbon, hydrocarbyloxycarbonyl, halogen, hydroxy or C.sub.1-6 alkoxy, or R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 may together represent the residue of a carbocyclic ring; R.sup.5 and R.sup.6 independently represent hydrogen, hydrocarbon, hydroxy or fluoro; R.sup.7 represents hydrogen or C.sub.1-3 alkyl; and R.sup.8 represents methyl or ethyl; which compounds are useful as anticonvulsant agents and in the treatment of neurodegenerative diseases.
Type:
Grant
Filed:
August 12, 1988
Date of Patent:
February 26, 1991
Assignee:
Merck Sharp & Dohme Ltd.
Inventors:
Raymond Baker, Paul D. Leeson, Susan F. Britcher
Abstract: The present invention provides a spiro-azabicyclic compound or a salt or prodrug thereof, said compound comprising a saturated or unsaturated 5-membered heterocyclic ring containing two heteroatoms selected from oxygen, nitrogen and sulphur, no more than one of said heteroatoms being nitrogen; said heterocyclic ring having a spiro attachment to an optionally substituted azabicyclo[2.2.1]heptane or azabicyclo[3.2.1]octane ring system; which compounds are useful for the treatment of neurological and mental disorders.
Type:
Grant
Filed:
June 29, 1989
Date of Patent:
February 12, 1991
Assignee:
Merck Sharp & Dohme, Ltd.
Inventors:
Raymond Baker, Leslie J. Street, John Saunders
Abstract: Compounds of formula III: ##STR1## wherein R.sup.1 is a 5- or 6-membered aromatic heterocyclic group; and R.sup.4 and R.sup.5 each idependently signify hydrogen, halogen, trifluoromethyl, cyano, nitro, amino or lower alkyl; are useful intermediates in a novel process for the preparation of a class of pharmacologically active compounds of formula I: ##STR2## wherein R.sup.1, R.sup.4 and R.sup.5 are as defined above; and R.sup.3 represents hydrogen or lower alkyl.
Type:
Grant
Filed:
September 29, 1989
Date of Patent:
December 11, 1990
Assignee:
Merck, Sharp & Dohme Ltd.
Inventors:
Peter G. Houghton, Stanley H. B. Wright
Abstract: The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted circle represents one or two double bonds in any position in the 5-membered ring;X, Y and Z independently represent oxygen, sulphur, nitrogen or carbon, provided that at least one of X, Y and Z represents oxygen, sulphur or nitrogen;A represents a group of formula II: ##STR2## in which R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, hydroxy(C.sub.1-6)alkyl, halogen, amino, cyano, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl;R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarbonyl;V represents nitrogen, ##STR3## and W represents oxygen, sulphur or ##STR4## in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.
Type:
Grant
Filed:
February 3, 1989
Date of Patent:
August 28, 1990
Assignee:
Merck Sharp & Dohme Ltd.
Inventors:
Raymond Baker, John Saunders, Christopher Swain
Abstract: Compounds of formula (I) and pharmaceutically acceptable acid addition salts thereof: ##STR1## wherein R represents a hydrocarbon group, X represents oxygen or sulphur, and R and --NH.sub.2 are cis; are of use in the treatment and/or prevention of neurodegenerative disorders, and are also useful as anticonvulsant agents and muscle relaxants.
Type:
Grant
Filed:
September 29, 1989
Date of Patent:
May 15, 1990
Assignee:
Merck Sharp & Dohme Ltd.
Inventors:
Raymond Baker, Paul D. Leeson, Tamara Ludduwahetty, Brian J. Williams
Abstract: Oral dosage forms for neutral, zwitterions or slats of acidic or basic drugs with approximate zero order release kinetics comprise a core matrix of the drug, and a gelling polymer, the matrix being coated with a water permeable but insoluble polymer.
Type:
Grant
Filed:
October 4, 1989
Date of Patent:
April 24, 1990
Assignee:
Merck Sharp & Dohme Ltd.
Inventors:
Claire J. Lovegrove, David A. Rawlins, Anthony J. Phillips, David A. Tainsh
Abstract: This invention provides the 4-mono-anion of myo-inositol orthoformate, and describes a process for preparing this anion as well as the use of this anion in the preparation of a variety of mono- and poly-phosphate derivatives of myo-inositol.