Patents by Inventor Michael D. Dowle

Michael D. Dowle 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: 7157494
    Abstract: The invention relates to compounds of general formula (I); in which R is an amino or guanidino group; R2 is acetyl or trifluoroacetyl; X is CONH, SO2NH, NHCO or NHCONH; m is either 0 or 1; n is an integer from 2 to 6; q is an integer from 0 to 3; and Y is hydrogen or an aromatic substituent, or a pharmaceutically acceptable derivative thereof; methods for their preparation, pharmaceutical formulations containing them or their use in the prevention or treatment of a viral infection
    Type: Grant
    Filed: November 8, 2002
    Date of Patent: January 2, 2007
    Assignee: Biota Scientific Management Pty. Ltd.
    Inventors: Michael D. Dowle, Betty Jin, Simon J. F. Macdonald, Andrew McM Mason, Darryl McConnell, Van T. T. Nguyen, Stephen E. Shanahan, Wen-Yang Wu
  • Patent number: 5498722
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt, solvate or metabolically labile ester thereof wherein the R groups are defined in the specification.The compounds may be used in the treatment or prophylaxis of hypertension and diseases associated with cognitive disorders.
    Type: Grant
    Filed: March 31, 1994
    Date of Patent: March 12, 1996
    Assignee: Glaxo Group
    Inventors: Barry C. Ross, David Middlemiss, David I. C. Scopes, Torquil I. M. Jack, Kevin S. Cardwell, Michael D. Dowle, Duncan B. Judd, Stephen P. Watson
  • Patent number: 5374646
    Abstract: The invention provides compounds of the general formula (I) ##STR1## and physiologically acceptable salts, solvates or non-toxic metabolically labile esters thereof where R.sup.1 represents a halogen atom; Ar represents the group ##STR2## R.sup.3 represents a C-linked tetrazolyl group; R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom or a C.sub.1-6 alkyl group; andHet represents an N-linked imidazolyl group optionally substituted at the 2-position.The compounds may be used in the treatment or prophylaxis of hypertension and diseases associated with cognitive disorders.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: December 20, 1994
    Assignee: Glaxo Group Limited
    Inventors: Barry C. Ross, David Middlemiss, David I. C. Scopes, Torquil I. M. Jack, Kevin S. Cardwell, Michael D. Dowle
  • Patent number: 5332831
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt, solvate or metabolically labile ester thereof whereinAr represents the group ##STR2## wherein R.sup.3 represents an acidic group selected from --CO.sub.2 H, --NHSO.sub.2 CF.sub.3 or a C-linked tetrazolyl group;Het represents the group ##STR3## with all other undefined groups being defined in the specification. The compounds may be used in the treatment or prophylaxis of hypertension and diseases associated with cognitive disorders.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: July 26, 1994
    Assignee: Glaxo Group Limited
    Inventors: Michael D. Dowle, Duncan B. Judd
  • Patent number: 5317023
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt, solvate or metabolically labile ester thereof whereinR.sup.1 represents a hydrogen atom or a halogen atom or a group selected from C.sub.1-6 alkyl, C.sub.2-6 alkenyl, fluoroC.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CHO, --CO.sub.2 H or --COR.sup.2 ;Ar represents optionally substituted phenylHet represents the group ##STR2## A represents ##STR3## The compounds may be used in the treatment or prophylaxis of hypertension and diseases associated with cognitive disorders.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: May 31, 1994
    Assignee: Glaxo Group Limited
    Inventors: Barry C. Ross, David Middlemiss, David I. C. Scopes, Torquil I. M. Jack, Kevin S. Cardwell, Michael D. Dowle, John G. Montana, Martin Pass, Duncan B. Judd
  • Patent number: 5310927
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt, solvate or metabolically labile ester thereof whereinR.sup.1 represents a hydrogen atom or a halogen atom or a group selected from C.sub.1-6 alkyl, C.sub.2-6 alkenyl, fluoroC.sub.1-6 alkyl, C.sub.1-6 alkoxy, --CHO, --CO.sub.2 H or --COR.sup.2 ;Ar represents the group ##STR2## Het represents an N-linked imidazolyl group optionally substituted by one, two or three substituents.The compounds may be used in the treatment or prophylaxis of hypertension and diseases associated with cognitive disorders.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: May 10, 1994
    Assignee: Glaxo Group Limited
    Inventors: Barry C. Ross, David Middlemiss, David I. C. Scopes, Torquil I. M. Jack, Kevin S. Cardwell, Michael D. Dowle, Duncan B. Judd
  • Patent number: 5252593
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt, solvate or metabolically labile ester thereof.The compounds may be used in the treatment or prophylaxis of hypertension and diseases associated with cognitive disorders.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: October 12, 1993
    Assignee: Glaxo Group Limited
    Inventors: Barry C. Ross, David Middlemiss, David I. C. Scopes, Torquil I. M. Jack, Kevin S. Cardwell, Michael D. Dowle, Colin D. Eldred, John G. Montana, Pritom Shah, Stephen P. Watson
  • Patent number: 5023378
    Abstract: The invention provides compounds of the general formula (I) ##STR1## and physiologically acceptable acid addition salts, metabolically labile esters and solvates thereof in whichR.sup.1 represents a halogen atom or a methyl, ethyl, n-propyl or n-butyl group;R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each represent hydrogen atoms or one or two of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 represent a methy or ethyl group;X represents a C.sub.4-7 alkylene chain optionally substituted by one or more C.sub.1-4 alkyl or hydroxyl groups; or optionally containing one or two double or triple bonds; or optionally interrupted by an oxygen or sulphur atom, or by a sulphone (--SO.sub.2 --) or urea (--NHCONH--) group; andY represents a phenyl ring optionally carrying one to three substituents selected from hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino, carboxamido, C.sub.1-4 alkylsulphonylamino and nitro groups and halogen atoms with the proviso that when X is a C.sub.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: June 11, 1991
    Assignee: Glaxo Group Limited
    Inventors: Michael D. Dowle, David Middlemiss, Harry Finch, Alan Naylor, Lawrence H. C. Lunts
  • Patent number: 4994483
    Abstract: Indole derivatives are disclosed of the general formula (I): ##STR1## wherein R.sub.1 is hydrogen, C.sub.1-6 alkyl or C.sub.3-6 alkenyl; R.sub.2 is a hydrogen, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, phenyl, phen(C.sub.1-4)alkyl or C.sub.5-7 cycloalkyl; R.sub.3 and R.sub.4 are hydrogen, C.sub.1-3 alkyl or propenyl groups or together form an aralkylidene group; Alk is C.sub.2 -C.sub.3 alkylene chain and A is C.sub.2 -C.sub.5 alkylene chainand its physiologically acceptable salts and solvates.The compounds may be prepared, for example, by cyclization of a compound of general formula (II): ##STR2## where Q is the group NR.sub.3 R.sub.4 or a protected derivative thereof or a leaving group and R.sub.1 l, R.sub.2, R.sub.3, R.sub.4, A and Alk are as defined for formula (I).The compounds have a selective vosoconstrictor action and are useful in treating pain such as migraine. The compounds may be formulated as pharmaceutical compositions in conventional manner, preferably for oral administration.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: February 19, 1991
    Assignee: Glaxo Group Limited
    Inventors: Alexander W. Oxford, Brian Evans, Michael D. Dowle, Ian H. Coates
  • Patent number: 4894387
    Abstract: Compounds are disclosed of the general formula (I) ##STR1## wherein R.sub.1 represents halogen, alkyl, alkoxy or hydroxyl, or a group NR.sub.a R.sub.b or CON.sub.a R.sub.b, where R.sub.a and R.sub.b are hydrogen, alkyl or alkenyl or with the nitrogen atom form a saturated monocyclic 5 to 7-membered ring;R.sub.2 represents hydrogen or alkyl;R.sub.3 and R.sub.4 represent hydrogen, C.sub.1-3 alkyl or propenyl or R.sub.3 and R.sub.4 together form an aralkylidene group; Alk represents a C.sub.2-3 alkylene chain;n and m, are integers of 1 to 4 or n is zero, and their physiologically acceptable salts and solvates.The compounds are described as useful in treating pain originating from dilatation of the cranial vasculature in particular migraine and cluster headache and can be formulated in conventional manner as pharmaceutical compositions with carriers or excipients for administration by any convenient route.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: January 16, 1990
    Assignee: Glaxo Group Limited
    Inventors: Darko Butina, Michael D. Dowle, Ian H. Coates
  • Patent number: 4876267
    Abstract: Indole derivatives are disclosed of the formula (I): ##STR1## wherein R.sub.1 represents H, or C.sub.1-6 alkyl or C.sub.3-6 Alkenyl;R.sub.2 represents a H, C.sub.1-3 alkyl, C.sub.3-6 alkenyl or C.sub.5-7 cycloalkyl, or a phenyl or phen(C.sub.1-4)alkyl group in which the phenyl ring is optionally substituted by halogen or C.sub.1-3 alkyl, C.sub.1-3 alkoxy or hydroxyl, or by a group NR.sup.a R.sup.b, or CONR.sup.a R.sup.b, wherein R.sup.a and R.sup.b each independently represents H or C.sub.1-3 alkyl;R.sub.3 and R.sub.4, each independently represents H or C.sub.1-3 alkyl or 2-propenyl;and physiologically acceptable salts and solvates (e.g. hydrates) thereof.The compounds have potent and selective vasoconstrictor activity and are indicated as useful for the treatment of migraine. The compounds may be formulated as pharmaceutical compositions with pharmaceutically acceptable carriers or excipients for administration by any suitable means. Various methods for the preparation of the compounds are disclosed.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: October 24, 1989
    Assignee: Glaxo Group Limited
    Inventors: Darko Butina, Michael D. Dowle, David E. Bays, Colin F. Webb
  • Patent number: 4855314
    Abstract: Compounds are disclosed of formula (I): ##STR1## wherein R.sub.1 is halogen, a C.sub.1-3 alkoxy, R.sub.6 R.sub.7 NCO(CH.sub.2).sub.p --, R.sub.6 CONH(CH.sub.2).sub.p --, R.sub.6 R.sub.7 NSO.sub.2 (CH.sub.2).sub.p --, or R.sub.8 SO.sub.2 NH(CH.sub.2).sub.p -- (where R.sub.6 and R.sub.7 each represents hydrogen or C.sub.1-3 alkyl, R.sub.8 represents C.sub.1-3 alkyl and p is zero or 1);R.sub.2 represents hydrogen or C.sub.1-3 alkyl; R.sub.3 represents hydrogen or C.sub.1-3 alkyl;R.sub.4 and R.sub.5 each represents hydrogen, C.sub.1-3 alkyl or 2-propenyl;A represents --CO-- or --SO.sub.2 --;n represents an integer from 2 to 5; and m represents zero or an integer from 1 to 4; and physiologically acceptable salts and solvates (e.g. hydrates) thereof.The compounds have potent and selective vasoconstrictor activity and are indicated as useful for the treatment of migraine.
    Type: Grant
    Filed: January 8, 1987
    Date of Patent: August 8, 1989
    Assignee: Glaxo Group Limited
    Inventors: Alexander W. Oxford, Ian H. Coates, David E. Bays, Colin F. Webb, Michael D. Dowle, Keith Mills, Colin D. Eldred
  • Patent number: 4839377
    Abstract: Compounds are disclosed of general formula (I) ##STR1## wherein R.sub.1 represents a group CHO, COR.sub.8, CO.sub.2 R.sub.8, CONR.sub.9 R.sub.10, CSNR.sub.9 R.sub.10 or SO.sub.2 NR.sub.9 R.sub.10,where R.sub.8 represents an alkyl, cycloalkyl, aryl or aralkyl group,R.sub.9 represents a hydrogen atom or an alkyl group, andR.sub.10 represents a hydrogen atom or an alkyl, cyclo-alkyl, aryl or aralkyl group;R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom or a C.sub.1-3 alkyl group;R.sub.5 represents a hydrogen atom or an alkyl, cycloalkyl, alkenyl or an aralkyl group orR.sub.4 and R.sub.5 together form an aralkylidene group orR.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a saturated monocyclic 5- to 7-membered ring; andAlk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C.sub.1-3 alkyl groups;with the provisos that when R.sub.
    Type: Grant
    Filed: August 6, 1987
    Date of Patent: June 13, 1989
    Assignee: Glaxo Group Limited
    Inventors: David E. Bays, Colin F. Webb, Michael D. Dowle
  • Patent number: 4833153
    Abstract: Compounds are disclosed of formula (I): ##STR1## wherein one of R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-6 alkyl C.sub.3-6 alkenyl, hydroxy, C.sub.1-4 alkoxy or a C.sub.2-5 alkoxycarbonyl group, a phenyl or substituted phenyl group or a phen(C.sub.1-4)alkyl or substituted phen(C.sub.1-4)alkyl group; and the other two each independently represents hydrogen, C.sub.1-6 alkyl, or R.sup.2 and R.sup.3 together form an alkylene chain --(CH.sub.2).sub.n --where n is 2 or 3, bridging the nitrogen atoms to which they are attached; R.sup.4 and R.sup.5, each independently represents hydrogen, C.sub.1-3 alkyl or propenyl; R.sup.6 represents hydrogen, C.sub.1-3 alkyl, and the physiologically acceptable salts and solvates thereof.The compounds (I) have potent and selective vasoconstrictor activity and are potentially useful for the treatment of migraine. The compounds (I) may be formulated in conventional manner as pharmaceutical compositions for administration by any convenient route.
    Type: Grant
    Filed: November 7, 1986
    Date of Patent: May 23, 1989
    Assignee: Glaxo Group Limited
    Inventors: Michael D. Dowle, Brian Evans, Peter Clark
  • Patent number: 4816470
    Abstract: Indole derivatives of the general formula (I) are disclosed: ##STR1## where R.sub.1 is H or an alkyl or alkenyl group, R.sub.2 is H, or an alkyl, alkenyl, aryl, aralkyl or cycloalkyl group;R.sub.3 is H or an alkyl group;R.sub.4 and R.sub.5 are independently H or an alkyl or propenyl group or together form an aralkylidene group; andAlk is an optionally substituted alkylene chain; and their physiologically acceptable salts and solutes.These compounds are potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner.Various methods for the production of the compounds are disclosed including a Fischer-indole cyclization process.
    Type: Grant
    Filed: November 15, 1985
    Date of Patent: March 28, 1989
    Assignee: Glaxo Group Limited
    Inventors: Michael D. Dowle, Ian H. Coates
  • Patent number: 4795756
    Abstract: Compounds are disclosed of formula (I) ##STR1## wherein R.sub.1 is H, C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, phenyl optionally substituted by C.sub.1-3 alkoxy or phen(C.sub.1-4) alkyl in which the phenyl ring is optionally substituted by C.sub.1-3 alkoxy;R.sub.2 is H or C.sub.1-6 alkyl;R.sub.3 is H or C.sub.1-3 alkyl;R.sub.4 and R.sub.5 independently represents H, C.sub.1-3 alkyl or 2-propenyl; andn represents zero or 1;and physiologically acceptable salts and solvates (e.g. hydrates) thereof.The compounds have potent selective vasoconstrictor activity and are indicated as useful for the treatment of migraine. The compounds may be formulated as pharmaceutical compositions with physiologically acceptable carrier or excipients for administration by any convenient route. Various methods for the preparation of the compounds (I) are disclosed.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: January 3, 1989
    Assignee: Glaxo Group Limited
    Inventors: Alexander W. Oxford, Michael D. Dowle
  • Patent number: 4672067
    Abstract: Compounds are disclosed of formula (I) ##STR1## wherein R.sub.1 represents CHO, COR.sub.8, CO.sub.2 R.sub.8, CONR.sub.9 R.sub.10, CSNR.sub.9 R.sub.10 or SO.sub.2 NR.sub.9 R.sub.10, whereR.sub.8 represents alkyl, cycloalkyl, aryl or aralkyl,R.sub.9 represents hydrogen or alkyl, andR.sub.10 represents hydrogen or alkyl, cycloalkyl, aryl or aralkyl;R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7 each independently represents hydrogen or C.sub.1-3 alkyl;R.sub.5 represents hydrogen, or alkyl, cycloalkyl, alkenyl or aralkyl, orR.sub.4 and R.sub.5 together form an aralkylidene group or R.sub.4 and R.sub.5 together with the attached nitrogen atom form a saturated monocyclic 5- to 7-membered ring; andAlk represents C.sub.2-3 alkylene chain optionally substituted by not more than two C.sub.1-3 alkyl groups;and physiologically acceptable salts and solvates thereof.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: June 9, 1987
    Assignee: Glaxo Group Limited
    Inventors: Ian H. Coates, Keith Mills, Colin F. Webb, Michael D. Dowle, David E. Bays
  • Patent number: 4650810
    Abstract: Compounds are disclosed of general formula (I): ##STR1## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom or an alkyl group;R.sub.2 represents a hydrogen atom or an alkyl, aryl, aralkyl, cycloalkyl or alkenyl group;or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, form a saturated monocyclic 5 to 7-membered ring which may optionally contain a further hetero function;R.sub.5 represents a hydrogen atom or an alkyl or alkenyl group;or R.sub.4 and R.sub.5 together form an aralkylidene group;Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C.sub.1-3 alkyl groups; andX represents an oxygen or sulphur atom; and physiologically acceptable salts, solvates and bioprecursors thereof.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: March 17, 1987
    Assignee: Glaxo Group Limited
    Inventors: David E. Bays, Colin F. Webb, Michael D. Dowle
  • Patent number: 4636521
    Abstract: Compounds are disclosed of general formula (I) ##STR1## wherein R.sub.1 represents an alkyl, cycloalkyl, aryl or aralkyl group;R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom or a C.sub.1-3 alkyl group;R.sub.5 represents a hydrogen atom or an alkyl, cycloalkyl, alkenyl or an aralkyl group; or R.sub.4 and R.sub.5 together form an aralkylidene group or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a saturated monocyclic 5- to 7-membered ring; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C.sub.1-3 alkyl groups; and physiologically acceptable salts, solvates and bioprecursors thereof. The compounds are described as potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner using one or more pharmaceutically acceptable carriers or excipients.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: January 13, 1987
    Assignee: Glaxo Group Limited
    Inventors: Ian H. Coates, Keith Mills, Colin F. Webb, Michael D. Dowle, David E. Bays
  • Patent number: 4239769
    Abstract: Compounds of the general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof are disclosed, in whichR.sub.1 and R.sub.2, which may be the same or different, represent hydrogen, lower alkyl, cycloalkyl, aralkyl or lower alkenyl groups, which alkyl groups may be interrupted by an oxygen atom or a group ##STR2## in which R.sub.4 represents hydrogen or lower alkyl; or R.sub.1 and R.sub.2 may, together with the nitrogen atom to which they are attached form a heterocyclic ring which may contain other hetero functions selected from --O-- and ##STR3## R.sub.3 represents hydrogen, lower alkyl, lower alkenyl or alkoxyalkyl; X represents --O--, --S-- or --CH.sub.2 --;Y represents .dbd.S, .dbd.O, .dbd.NR.sub.5 or .dbd.CHR.sub.6 ;in which R.sub.5 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl and R.sub.6 represents nitro, alkylsulphonyl or arylsulphonyl;m is an integer from 2 to 4 inclusive;n is 1 or 2 or, when X is S or CH.sub.
    Type: Grant
    Filed: May 5, 1978
    Date of Patent: December 16, 1980
    Assignee: Allen & Hanburys Limited
    Inventors: Barry J. Price, John W. Clitherow, Michael D. Dowle, Roger Hayes, John Bradshaw