Patents by Inventor Michael S. Hadley

Michael S. Hadley has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5523299
    Abstract: Compounds of formula (I), ##STR1## wherein R.sup.1 represents C.sub.1-4 alkyl; and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently represent hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, C.sub.1-4 alkylsulphonyl, trifluoromethylsulphonyl; optionally substituted arylsulphonyl, optionally substituted heteroarylsulphonyl, optionally substituted aralkylsulphonyl, optionally substituted heteroaralkylsulphonyl, nitro, cyano, amino, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxyalkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl; or R.sup.1 and R.sup.2 together form a linking chain-(CH.sub.2).sub.m Op (wherein m is 2 to 4 and p is zero or 1) which chain may be optionally substituted by one or two C.sub.1-4 alkyl groups; and Y represents a group selected from (a) or (b) wherein R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: June 4, 1996
    Assignee: SmithKline Beecham PLC
    Inventors: Geoffrey Stemp, Michael S. Hadley, David J. Nash, Christopher N. Johnson
  • Patent number: 5189047
    Abstract: The present invention is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein Y, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 , a and b are as defined in the Specification, having pharmacological activity, to a process for their preparation, and to their use as pharmaceuticals.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: February 23, 1993
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Graham E. Jones
  • Patent number: 5132316
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents R.sub.1 OOC-- in which R.sub.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl; R.sub.2 O-- in which R.sub.2 is C.sub.1-2 alkyl, C.sub.1 -2 alkylcarbonyl or aminocarbonyl optionally substituted by one or two methyl groups;a group ##STR2## in which Y represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-2 alkyl group, Y being optionally C-substituted by a methyl group; ora group ##STR3## in which A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.3 and the other is nitrogen or CR.sub.4 where R.sub.3 and R.sub.4 are independently selected from hydrogen and methyl; and each of p and q independently represents an integer of 2 to 4.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: July 21, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Paul A. Wyman, Barry S. Orlek
  • Patent number: 5110828
    Abstract: Novel compounds of formula (I), a process for their preparation, and their use as pharmaceutical agents are described: ##STR1## wherein R.sub.1 represents ##STR2## in which each of p and q independently represents an integer of 2 to 4, r represents an integer of 2 to 4, s represents 1 or 2 and t represents 0 or 1;R.sub.2 is a group OR.sub.4, where R.sub.4 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, a group OCOR.sub.5 where R.sub.5 is hydrogen or R.sub.4, or a group NHR.sub.6 or NR.sub.7 R.sub.8 where R.sub.6, R.sub.7 and R.sub.8 are independently C.sub.1-2 alkyl; andR.sub.3 is hydrogen or C.sub.1-4 alkyl, subject to the proviso that when R.sub.2 is a group OCOR.sub.5 or a group NHR.sub.6, R.sub.3 is C.sub.1-4 alkyl.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: May 5, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Steven M. Bromidge, Michael S. Hadley, Barry S. Orlek
  • Patent number: 5091397
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which one of X and Y represents hydrogen and the other represents --CH.sub.2 --Z where Z is a group ##STR2## in which Q represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, or three nitrogen atoms, any amino nitrogen being optionally substituted by a C.sub.1-2 alkyl, cyclopropyl or propargyl group, and any ring carbon atom being optionally substituted by a group R.sub.1 ; or a group ##STR3## in which A.sub.1, A.sub.2 and A.sub.3 complete a 5-membered aromtic ring and A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.2 and the other is nitrogen or CR.sub.3, or A.sub.2 is oxygen or sulphur, one of A.sub.1 and A.sub.3 is CR.sub.2 and the other is CR.sub.3 ; and R.sub.1, R.sub.2 and R.sub.3 are independently selected from hydrogen, halogen, CN, OR.sub.4, SR.sub.4, N(R.sub.4).sub.2, NHCOR.sub.4, NHCOOCH.sub.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: February 25, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Harry J. Wadsworth, Michael S. Hadley, Paul A. Wyman, Sarah M. Jenkins
  • Patent number: 5043342
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1##
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: August 27, 1991
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Paul A. Wyman, Barry S. Orlek
  • Patent number: 4988706
    Abstract: Novel compounds of formula (I), processes for their preparation, and their use as pharmaceutical agents are described: ##STR1## in which X represents a group ##STR2## wherein one of Y and Z represents nitrogen and the other represents CR where R is selected from halogen, CN, OR.sup.1, SR.sup.1, N(R.sup.1).sub.2, NHR.sup.1, NHCOR.sup.1, NHCOOCH.sub.3, NHCOOC.sub.2 H.sub.5, NHOR.sup.1, NHNH.sub.2, COR.sup.1, COR.sup.2, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl or C.sub.1-2 alkyl substituted with OR.sup.1, N(R.sup.1).sub.2, SR.sup.1, CO.sub.2 R.sup.1, CON(R.sup.1).sub.2 or one or two halogen atoms, in which R.sup.1 is hydrogen or C.sub.1-2 alkyl and R.sup.2 is OR.sup.1, NH.sub.2 or NHR.sup.1 ; and each of p and q independently represents an integer of 2 to 4.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: January 29, 1991
    Assignee: Beecham Group P.L.C.
    Inventors: Michael S. Hadley, Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth
  • Patent number: 4971975
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents R.sub.1 OOC-- in which R.sub.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl; R.sub.2 O-- in which R.sub.2 is C.sub.1-2 alkyl, C.sub.1-2 alkylcarbonyl or aminocarbonyl optionally substituted by one or two methyl groups;a group ##STR2## in which Y represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-2 alkyl group, Y being optionally C-substituted by a methyl group; or a group ##STR3## in which A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.3 and the other is nitrogen or CR.sub.4 where R.sub.3 and R.sub.4 are independently selected from hydrogen and methyl; and each of p and q independently represents an integer of 2 to 4.
    Type: Grant
    Filed: April 15, 1988
    Date of Patent: November 20, 1990
    Assignee: Beecham Group plc
    Inventors: Michael S. Hadley, Paul A. Wyman, Barry S. Orlek
  • Patent number: 4968691
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which X represents a group ##STR2## in which p represents an integer of 2 to 4; r represents an integer of 1 or 2; s represents 0 or 1; and A represents a 3-membered divalent residue completing a 5-membered aromatic ring and comprises one or two heteroatoms selected from oxygen, nitrogen and sulphur, any amino nitrogen optionally substituted by a C.sub.1-4 alkyl group, and when (p,r,s) is (2,2,0) or (2,2,1) any A comprising 2 heteroatoms is optionally C-substituted by a methyl group, and when (p,r,s) is (2,1,0), (2,1,1) or (3,1,0) any A comprising 2 heteroatoms is optionally C-substituted by C.sub.1-2 alkyl and any A comprising one heteroatom is optionally C-substituted by a methyl group, and wherein compounds of formula (I) having two asymetric centers have the stereo-chemical configuration in which the group X and the (CH.sub.2).sub.
    Type: Grant
    Filed: March 7, 1989
    Date of Patent: November 6, 1990
    Assignee: Beecham Group P.L.C.
    Inventors: Barry S. Orlek, Michael S. Hadley, Howard E. Rosenberg, Harry J. Wadsworth
  • Patent number: 4883874
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: j is 0 or 1;q is 0, 1 or 2;p is 0 and r is 2 or 3, orp is 1 and r is 2;X is O, S, SO or NR where R is hydrogen, C.sub.1-6 alkyl or C.sub.1-10 carboxylic acyl;Y is NH; or O when R.sub.1 is hydrogen;either R.sub.1-6 alkoxy and one of R.sub.2, R.sub.3 and R.sub.4 is hydrogen and the other two are selected from hydrogen, halogen, CF.sub.3, C.sub.1-6 alkylithio, C.sub.1-7 acyl, C.sub.1-10 carboxylic acylamino, C.sub.1-6 alkyl S(O)n wherein n is 0, 1 or 2, nitro or amino, aminocarbonyl or aminosulphonyl optionally substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl groups any of which phenyl moieties may be substituted by one or two groups selected from halogen, CF.sub.3, C.sub.1-6 alkyl or C.sub.1-6 alkoxy; or R.sub.1 is hydrogen and R.sub.2, R.sub.3 and R.sub.4 are independently selected from hydrogen, C.sub.
    Type: Grant
    Filed: February 8, 1989
    Date of Patent: November 28, 1989
    Assignee: Beecham Group plc. of Beecham House
    Inventors: Francis D. King, Michael S. Hadley, Roger T. Martin
  • Patent number: 4870081
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## in which A represents a bond or --CH.sub.2 -- and B represents hydrogen, or A and B together with the carbon atom to which they are both attached represents a group ##STR2## R represents R.sub.1 OOC-- in which R.sub.1 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkynyl; R.sub.2 O-- in which R.sub.2 is C.sub.1-3 alkyl, C.sub.1-2 alkylcarbonyl or aminocarbonyl optionally substituted by one or two methyl groups; or R.sub.3 CH.sub.2 - in which R.sub.3 is C.sub.1-2 alkoxy; and p represents an integer of 2 to 4, and wherein compounds of formula (I) where B is hydrogen have the stereochemical configuration in which the group R and the methylene bridge are both on the same side of the plane of the molecule which contains both bridge head atoms and the ring carbon atom bonded to the group R.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: September 26, 1989
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Michael S. Hadley, Harry J. Wadsworth, Howard E. Rosenberg
  • Patent number: 4826839
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: j is 0 or 1;q is 0, 1 or 2;p is 0 and r is 2 or 3, orp is 1 and r is 2;X is O, S, SO or NR where R is hydrogen, C.sub.1-6 alkyl or C.sub.1-10 carboxylic acyl;Y is NH; or O when R.sub.1 is hydrogen; either R.sub.1 is C.sub.1-6 alkoxy and one of R.sub.2, R.sub.3 and R.sub.4 is hydrogen and the other two are selected from hydrogen, halogen, CF.sub.3, C.sub.1-6 alkylthio, C.sub.1-7 acyl, C.sub.1-10 carboxylic acylamino, C.sub.1-6 alkyl S(O) n wherein n is 0, 1 or 2, nitro or amino, aminocarbonyl or aminosulphonyl optionally substituted by one or two groups selected from C.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl C.sub.1-4 alkyl or phenyl C.sub.1-4 alkyl groups any of which phenyl moieties may be substituted by one or two groups selected from halogen, CF.sub.3, C.sub.1-6 alkyl or C.sub.1-6 alkoxy; or R.sub.1 is hydrogen and R.sub.2, R.sub.3 and R.sub.4 are independently selected from hydrogen, C.sub.
    Type: Grant
    Filed: July 17, 1986
    Date of Patent: May 2, 1989
    Assignee: Beecham Group p.l.c.
    Inventors: Francis D. King, Michael S. Hadley, Roger T. Martin
  • Patent number: 4719217
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein: R.sub.1 is C.sub.1-6 alkyl;R.sub.2 is amino or C.sub.1-7 acylamino;R.sub.3 is halo or C.sub.1-6 alkythio;R.sub.4 and R.sub.5 are independently selected from hydrogen, C.sub.1-6 alkyl, phenyl or phenyl C.sub.1-4 alkyl any of which phenyl moieties may be substituted by one or two of halo, CF.sub.3, C.sub.1-6 alkoxy or C.sub.1-6 alkyl;R.sub.6 is C.sub.1-7 alkyl, --(CH.sub.2).sub.s R.sub.7, s being 0 to 2 andR.sub.7 being C.sub.3-8 cycloalky, --(CH.sub.2).sub.t R.sub.8, t being 1 or 2 andR.sub.8 being thienyl or phenyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy and C.sub.1-4 alkyl optionally substituted by hydroxy, C.sub.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: January 12, 1988
    Assignee: Beecham Group p.l.c.
    Inventors: Francis D. King, Michael S. Hadley
  • Patent number: 4705858
    Abstract: Certain endo-9-lower-alkyl 9-azabicyclo[3.3.1]nonane-3-amines are valuable intermediates for the preparation of 2-methoxy-4-amino-5-halo-N-[9-lower-alkyl]-azabicyclo[3.3.1]nonanylbenzami des wherein said final products possess useful pharmacological activity, such as ability to regulate gastro-intestinal function, anti-emetic activity and CNS activity.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: November 10, 1987
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Francis D. King
  • Patent number: 4599420
    Abstract: This invention relates to novel substituted benzamides having useful pharmacological properties, to pharmaceutical compositions containing them, to a process for their preparation and to intermediates therefor.N-(2-Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide, 1-ethyl-2(2-methoxy-5-sulphamoylbenzamidomethyl)pyrrolidine and N-[4'-(1"-benzyl)-piperidyl]-2-methoxy-4-amino-5-chlorobenzamide are well known compounds having useful pharmacological activity such as the ability to regulate the gastro-intestinal function anti-emetic activity and CNS activity.It has now been found that certain intermediates for a structurally distinct class of substituted benzamides also has useful pharmacological activity, in particular dopamine antagonist activity.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: July 8, 1986
    Assignee: Beecham Group Ltd.
    Inventors: Michael S. Hadley, Francis D. King
  • Patent number: 4560757
    Abstract: Compounds of formula (I): ##STR1## wherein X is methoxy or ethoxy, Y is amino or C.sub.1-6 alkanoylamino, Z is hydrogen, chloro or bromo and R.sub.1 is methyl, chloro or fluoro, have anti-psychotic activity, and are useful in the treatment of CNS disorders. Intermediates for the above compounds are also disclosed.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: December 24, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Francis E. Blaney
  • Patent number: 4544660
    Abstract: A compound of the formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sub.1 is a C.sub.1-6 alkoxy group;R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, CF.sub.3, C.sub.2-7 acyl, C.sub.2-7 acylamino, or amino, aminocarbonyl or aminosulphone optionally substituted by one or two C.sub.1-6 alkyl groups, C.sub.1-6 alkylsulphone or nitro;R.sub.5 is hyrogen or C.sub.1-6 alkyl;R.sub.6 is C.sub.1-7 alkyl or a group --(CH.sub.2).sub.s R.sub.7 where s is 0 to 2 and R.sub.7 is a C.sub.3-8 cycloalkyl group, or a group --(CH.sub.2).sub.t R.sub.8 where t is 1 or 2 and R.sub.8 is C.sub.2-5 alkenyl or a phenyl group optionally substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-4 alkoxy, trifluoromethyl and halogen; andn, p and q are independently 0 to 2; have useful pharmacological activity.
    Type: Grant
    Filed: June 9, 1981
    Date of Patent: October 1, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Francis D. King
  • Patent number: 4533498
    Abstract: Compounds of formula (I), pharmaceutically acceptable salts, quaternary derivatives and N-oxides thereof, and pharmaceutically acceptable solvates of any of the foregoing: ##STR1## wherein p is 1 to 3;B is C.sub.1-7 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, or a group (CH.sub.2).sub.t R.sub.11 where t is 1 or 2 and R.sub.11 is thienyl or furyl optionally substituted or is phenyl optionally substituted; and(i) A is a group of formula (II): ##STR2## in which either (a) one of X and Y is CO and the other is NH; or X is CO and Y is NR.sub.6 ; and or(b) one of X and Y is CO and the other is NH; or(ii) A is a group of formula (III): ##STR3## in which one of X and Y is CO and the other is NH, having useful pharmacological properties, pharmaceutical compositions containing them, a process and intermediates for their preparation, and the use of the compounds.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: August 6, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Francis E. Blaney, Michael S. Hadley, Francis D. King, Eric A. Watts
  • Patent number: 4480099
    Abstract: A compound of formula (I), and salts thereof: ##STR1## wherein: R.sub.1 is a C.sub.1-6 alkoxy group;R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, CF.sub.3, C.sub.1-7 acyl, amino, C.sub.1-7 acyl amino, aminocarbonyl or aminosulphone optionally substituted by one or two C.sub.1-6 alkyl groups; C.sub.1-6 alkyl-SO.sub.n wherein n is 1 or 2; or nitro;R.sub.4 is hydrogen or C.sub.1-6 alkyl;R.sub.5 is C.sub.1-6 alkyl or a group --(CH.sub.2).sub.s R.sub.6 wherein s is 1 or 2 and R.sub.6 is C.sub.3-8 cycloalkyl or phenyl, which phenyl may optionally be substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-4 alkoxy, CF.sub.3 and halogen;n is 0 to 3;p is 3 to 6; andr plus s is 2 to 5; may be used for the treatment of disorders of the gastro-intestinal function.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: October 30, 1984
    Assignee: Beecham Group P.L.C.
    Inventor: Michael S. Hadley
  • Patent number: 4472413
    Abstract: Compounds of formula (I): ##STR1## wherein X is methoxy or ethoxy, Y is amino or C.sub.1-6 alkanoylamino, Z is hydrogen, chloro or bromo and R.sub.1 is methyl, chloro or fluoro, have anti-psychotic activity, and are useful in the treatment of CNS disorders.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: September 18, 1984
    Assignee: Beecham Group p.l.c.
    Inventors: Michael S. Hadley, Francis E. Blaney