Patents Assigned to ICI Pharma
  • Patent number: 5278177
    Abstract: The invention concerns a bicyclic heterocyclic derivative of the formula I ##STR1## wherein Q is an optionally substituted 9-membered bicyclic heterocyclic moiety containing 1 or 2 N's and optionally a further N, O or S heteroatom;A.sup.1 is a direct link to X.sup.1 or 1- 3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or pyridylene;R.sup.1 is (1- 4C)alkyl, (3- 4C)alkenyl or (3- 4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1- 3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl; or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: January 11, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Pierre A. R. Bruneau, Graham C. Crawley, Keith Oldham
  • Patent number: 5276037
    Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: January 4, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5272173
    Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --wherein X.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: December 21, 1993
    Assignees: Imperial Chemical Industries PLC, Ici Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5262410
    Abstract: Cephalosporin compounds having a 3-position substituent of the formula (I) are described:--CH.sub.2 --S--Q--(Y).sub.n --Pwherein Q is a 5- or 6-membered heterocyclic ring, P is a benzene ring substituted by groups R.sup.1 and R.sup.2 which are ortho with respect to one another, wherein R.sup.1 is hydroxy or an in vivo hydrolysable ester thereof and R.sup.2 is hydroxy, an in vivo hydrolysable ester thereof, carboxy, sulpho, hydroxymethyl, methanesulphonamido or ureido; or P is a group of the formula (II) or (III): ##STR1## wherein M is oxygen or a group NR.sup.3 wherein R.sup.3 is hydrogen or C.sub.1-4 alkyl; said ring P being further optionally substituted; and --(Y).sub.n -- is a bond or various linking groups or --(Y)--.sub.n may be such so that rings Q and P are fused.The use of such compounds as antibacterial agents is described as are processes for their preparation and intermediates therefor.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: November 16, 1993
    Assignee: ICI Pharma
    Inventors: Frederic H. Jung, Annie A. Olivier
  • Patent number: 5260442
    Abstract: The invention concerns quinolinium salt intermediates of the formula I ##STR1## and processes for their manufacture; and their use in the manufacture of aryloxymethyl-substituted 1-alkyl-2-quinolone derivatives which are 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: December 5, 1991
    Date of Patent: November 9, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Jonathan Hutton, David Waterson
  • Patent number: 5258399
    Abstract: The invention concerns sulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 includes (1-4C)alkyl; R.sup.2 and R.sup.3 together form --A.sup.2 --X.sup.2 --A.sup.3 --which defines a ring having 5 to 7 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or Ar is pyridylene;Q is nitrogen or of the formula CR.sup.7, wherein R.sup.7 includes hydrogen, halogeno, (1-4C)alkyl and (1-4C)alkoxy;each of R.sup.4 and R.sup.5 is (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl or optionally substituted phenyl, benzyl or pyridyl, or R.sup.5 may be hydrogen; andR.sup.6 has any of the meanings defined for R.sup.7 ;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: November 2, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: David Waterson
  • Patent number: 5254679
    Abstract: A cephalosporin derivative of the formula I: ##STR1## in which X is S, O, CH.sub.2 or SO, ##STR2## represents one of C-7 acyl groups known in the cephalosporin art, R3 is hydrogen or methoxy, R4 is hydrogen, optionally substituted alkyl or allyl, and R5 is an aromatic heterocyclic ring system which is linked via carbon, and which contains a quaternized nitrogen atom.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: October 19, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: robert H. Bradbury, Frederic H. Jung, Jean J. Lohmann, Peter R. Marsham, Georges Pasquet
  • Patent number: 5254581
    Abstract: The invention concerns a cyclic ether derivative of the formula I ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a 9- or 10-membered bicyclic heterocyclic moiety;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar.sup.2 is optionally substituted phenylene or pyridylene;R.sup.1 includes hydrogen, (1-4C)alkyl, (1-4C)alkcxycarbonyl and (1-4C)alkylthio; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: February 2, 1993
    Date of Patent: October 19, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Pierre A. R. Bruneau, Robert I. Dowell, David Waterson
  • Patent number: 5240941
    Abstract: The invention concerns a thioxo heterocycle of the formula I ##STR1## wherein Q is a 10-membered bicyclic heterocyclic moiety containing 1 or 2 N's which bears 1 or 2 thioxo substituents and which is optionally further substituted;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or pyridylene;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: August 31, 1993
    Assignees: ICI Pharma, Imperial Chemical Industries PLC
    Inventor: Pierre A. R. Bruneau
  • Patent number: 5236948
    Abstract: The invention concerns sulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 includes (1-4C)alkyl;R.sup.2 and R.sup.3 together form --A.sup.2 --X.sup.2 --A.sup.3 -- which defines a ring having 5 to 7 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3 C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;A.sup.1 is a direct link to X.sup.1 or is (1-3 C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or Ar is pyridylene;Q is nitrogen or of the formula CR.sup.7, wherein R.sup.7 includes hydrogen, halogeno, (1-4 C)alkyl and (1-4 C)alkoxy;each of R.sup.4 and R.sup.5 is (1-4 C)alkyl, (3-4 C)alkenyl, (3-4 C)alkynyl or optionally substituted phenyl, benzyl or pyridyl, or R.sup.5 may be hydrogen; andR.sup.6 has any of the meanings defined for R.sup.7 ;or a pharmaceutically-acceptable salt thereof; processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: August 17, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: David Waterson
  • Patent number: 5236919
    Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents orAr is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.
    Type: Grant
    Filed: May 11, 1992
    Date of Patent: August 17, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
  • Patent number: 5234950
    Abstract: The invention concerns a heterocyclic derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo-(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X--A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-4C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: August 10, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Philip N. Edwards, Jean-Marc M. M. Girodeau
  • Patent number: 5232930
    Abstract: The invention concerns a benzodioxole derivative of the formula I ##STR1## wherein Ar.sup.1 is an optionally substituted 9- or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X--A.sup.2 -- which, together with the carbon atom to which A.sup.1 and A.sup.2 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X is oxy, thio, sulphinyl or sulphonyl, and which ring may bear one or two substituents;or a pharmaceutically-acceptable salt thereof;which compounds are inhibitors of 5-lipoxygenase and are useful in the treatment of inflammatory or allergic disease.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: August 3, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: John F. Kingston, David Waterson
  • Patent number: 5232918
    Abstract: Cephalosporin derivatives having a 3-position substituent of formula I are described: ##STR1## wherein R.sup.1 is hydrogen, alkenyl or optionally substituted alkyl, Het is a 5- or 6-membered heterocyclic ring bonded via a carbon atom to the amide linkage, wherein Het is selected from a group of the formulae II-III: ##STR2## wherein A is CH or a nitrogen atom; B is oxygen, sulphur or a group NR.sup.4 ; one or two of D, E, F and G are nitrogen atoms and the remainder are CH groups: or Het is a pyrazinone, pyridinone, pyridazinone or pyrimidinone ring, or is a thione equivalent of such a ring, said rings having a substituent R.sup.4 on one nitrogen atom, or is pyranone, or pyranthione; the ring Het being fused by any two adjacent carbon atoms to the benzene ring; and Het being attached to the --CH.sub.2 NR.sup.1 CO-- group via a carbon atom;R.sup.2 is hydroxy or an in vivo hydrolysable ester thereof;R.sup.3 is ortho to R.sup.2 and is hydroxy or an in vivo hydrolysable ester thereof; and R.sup.
    Type: Grant
    Filed: February 11, 1991
    Date of Patent: August 3, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Jean C. Arnould, Dominique Boucherot, David H. Davies, Frederick H. Jung, Colin J. Strawson
  • Patent number: 5229408
    Abstract: The invention concerns a 1,2-dihydro-3H-indazol-3-one derivative of formula I ##STR1## wherein R.sup.a is hydrogen, halogeno, hydroxy, cyano, trifluoromethyl, (1-6C)alkyl or (1-6C)alkoxy;R.sup.b is hydrogen or (1-6C)alkyl;R.sup.c is hydrogen, (1-8C)alkyl or (3-8C)alkenyl; andY is (1-8C)alkyl, (3-8C)alkenyl or (3-8C)alkynyl, or Y is a group of the formula --A--Q in which A is (1-6C)alkylene or (3-6C)alkenylene, and Q is phenyl or naphthyl, which may optionally bear one or two substituents;or a pharmaceutically-acceptable salt thereof;or a 1-(1-4C)alkoxycarbonyl derivative thereof.The invention also concerns processes for the manufacture of an indazol-3-one of the formula I and pharmaceutical compositions containing said indazol-3-one. Also included in the invention is a method of treating various inflammatory or allergic diseases using an indazol-3-one of the formula I.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: July 20, 1993
    Assignees: ICI PHARMA, Imperial Chemical Industries PLC
    Inventor: Pierre A. R. Bruneau
  • Patent number: 5221677
    Abstract: The invention concerns a heterocyclic derivative of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: June 22, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Philip N. Edwards
  • Patent number: 5219848
    Abstract: Cephalosporin antibiotics having a 3-position substituent of the formula: ##STR1## are described, wherein X is --CO--, --SO.sub.2 -- or --COCH.sub.2 --; Y is --CO--, --SO.sub.2 -- or --CH.sub.2 --; Q is a benzene, pyridine or naphthalene ring, R.sup.1 and R.sup.2 are ortho with respect to each other and are independently hydroxy or of the formula O--M wherein M is a moiety and the O--M bond is cleavable in vivo and ring Q may be further substituted by a variety of atoms and groups. Processes for their preparation and use are described.
    Type: Grant
    Filed: August 10, 1990
    Date of Patent: June 15, 1993
    Assignees: ICI Pharma, Imperial Chemical Industries PLC
    Inventors: Laurent F. A. Hennequin, David M. Hollinshead
  • Patent number: 5219881
    Abstract: The invention concerns a cyclic ether derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl or naphthyl;A.sup.1 is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo-(3-6C)alkylene;Ar.sup.2 is optionally substituted phenylene, or a 6 membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X--A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is (1-6C)alkylene and X is oxy, thio, sulphinyl, sulphonyl or imino; andR.sup.3 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: December 10, 1991
    Date of Patent: June 15, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: Annie Hamon
  • Patent number: 5217969
    Abstract: The invention concerns a bicyclic heterocyclic compound of the formula I ##STR1## wherein Q is an optionally substituted 10-membered bicyclic heterocyclic moiety containing 1 or 2 N's and a further O or S heteroatom;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or pyridylene;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl; or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: June 19, 1991
    Date of Patent: June 8, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Pierre A. R. Bruneau, Graham C. Crawley
  • Patent number: 5217977
    Abstract: The invention concerns a heterocyclic cycloalkane of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; and R.sup.2 and R.sup.3 together form a (3-6C)alkylene group which, together with the carbon atom to which R.sup.2 and R.sup.3 are attached, defines a ring having 4 to 7 ring atoms, and which ring may bear one or two substituents;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: June 8, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Jean-Marc M. M. Girodeau