Patents by Inventor Barry S. Orlek

Barry S. Orlek 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: 5541194
    Abstract: Novel compounds of formula (I), processes for their preparation, and their use as pharmaceutical agents are described: ##STR1## in which p represents an integer of 2 to 4; r represents an integer of 1 or 2; s represents 0 or 1; and X represents a group ##STR2## in which A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.1 and the other is nitrogen or CR.sub.2, or A.sub.2 is oxygen or sulphur, A.sub.1 is CH and A.sub.3 is CR.sub.1, where R.sub.1 and R.sub.2 are independently selected from hydrogen and C.sub.1-2 alkyl, with the proviso that when r is 2, R.sub.1 and R.sub.2 are hydrogen or methyl. The novel compounds of this invention may be used to treat or to prevent dementia in mammals.
    Type: Grant
    Filed: January 6, 1995
    Date of Patent: July 30, 1996
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth
  • Patent number: 5362739
    Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 represents ##STR2## and the remainder of the variables are defined in the specification are useful in the treatment and/or prophylaxis of dementia in mammals.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: November 8, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Steven M. Bromidge, Richard E. Faulkner, deceased
  • Patent number: 5356914
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sub.1 represents a 1,2,5,6-tetrahydropyridin-3-yl group N-substituted by R.sub.10 wherein R.sub.10 represents OH; a group hydrolysable in vivo to OH or hydrogen; C.sub.1-8 alkoxy; C.sub.2-8 alkenyloxy; C.sub.2-8 alkynyloxy; C.sub.3-8 cycloalkyloxy; or COR.sub.13 wherein R.sub.13 represents hydrogen, C.sub.1-8 alkyl, phenyl or phenyl C.sub.1-4 alkyl; in which any phenyl moiety is optionally substituted by up to 3 substituents independently selected from C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halo, C.sub.1-6 alkoxycarbonyl, cyano, C.sub.1-6 alkylthio or C.sub.1-6 alkylsulphonyl; enhance acetylcholine function via an action at muscarinic receptors within the central nervous system and are therefore of potential use in the treatment and/or prophylaxis of dementia in mammals.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: October 18, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Steven M. Bromidge, Barry S. Orlek, Steven Dabbs
  • Patent number: 5324724
    Abstract: Azabicyclic compounds, processes for their preparation and their use in the treatment and/or prophylaxis of dementia in animals.
    Type: Grant
    Filed: September 1, 1992
    Date of Patent: June 28, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Richard E. Faulkner
  • Patent number: 5314901
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R.sub.1 represents a 1,2,5,6-tetrahydropyridin-3-yl group N-substituted by R.sub.10 wherein R.sub.10 represents hydrogen, C.sub.1-2 alkyl, prop-2-enyl, prop-2-ynyl or cyclopropyl, 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; and R.sub.3 is chloro, fluoro, bromo, methoxy, C.sub.1-3 alkyl substituted by one, two or three halogen atoms, or R.sub.3 is a group (CH.sub.2).sub.n R.sub.9 where R.sub.9 is --CN, --SH or --SCH.sub.3 and n is 0 or 1, with the proviso that when n is 0, R.sub.9 is not --SH; enhance acetylcholine function via an action at muscarinic receptors within the central nervous system and are therefore of potential use in the treatment and/or prophylaxis of dementia in mammals.
    Type: Grant
    Filed: February 23, 1993
    Date of Patent: May 24, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Steven M. Bromidge, Barry S. Orlek, Steven Dabbs
  • Patent number: 5278170
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sup.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 chloro, fluoro, bromo, cyclopropyl, C.sub.1-3 alkyl substituted by one, two or three halogen atoms, or R.sub.3 is a group (CH.sub.2).sub.n R.sub.9 where R.sub.9 is --CN, --OH, --OCH.sub.3, --SH, --SCH.sub.3, --C.tbd.CH or --CH.dbd.CH.sub.2 and n is O or 1, with the proviso that when n is 0, R.sub.9 is not --OH or --SH.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: January 11, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Steven M. Bromidge, Steven Dabbs
  • Patent number: 5166357
    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 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 heteroatom selected from oxygen, nitrogen and sulphur or two heteroatoms selected from sulphur and nitrogen, any amino nitrogen being optionally substituted by a C.sub.1-2 alkyl, and at least one ring carbon atom being 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 aromatic ring and A.sub.1 is oxygen or sulphur, A.sub.2 is CR.sub.2 and A.sub.3 is nitrogen or CH, or A.sub.2 is oxygen or sulphur, A.sub.1 is CH and A.sub.3 is CR.sub.2 ; and R.sub.1 and R.sub.2 are selected from, halogen, CN, OR.sub.4, SR.sub.4, N(R.sub.4).sub.2, NHCOR.sub.4, NHCOOCH.sub.3, NHCOOC.sub.2 H.sub.5, NHOR.sub.4 NHNH.sub.2, NO.sub.2, COR.sub.4, COR.sub.5, C.sub.2-4 alkenyl, C.sub.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: November 24, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Richard E. Faulkner
  • 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: 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: 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: 4638066
    Abstract: Compounds of formula (I), ##STR1## or an N-oxide or pharmaceutically acceptable salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-7 alkyl, C.sub.3-7 cycloalkyl, C.sub.4-7 cycloalkenyl or C.sub.1-4 alkyl substituted by C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, C.sub.3-7 cycloalkyl, hydroxy, thiol, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, carboxy, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkanoyl, amino optionally substituted by one or two C.sub.1-4 alkyl or by C.sub.4-6 polymethylene optionally containing an oxygen or nitrogen atom, aminocarbonyl optionally N-substituted by one or two C.sub.1-4 alkyl, or benzoyl or phenyl either being optionally ring-substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or trifluoromethyl, R.sub.2 and R.sub.3 are the same or different and are hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halogen or trifluoromethyl, m is 1 to 3 and n is 1 or 2, the hydrogen atom bonded to the C.sub.a carbon atom being trans to the hydrogen atom bonded to the C.sub.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: January 20, 1987
    Assignee: Beecham Group p.l.c.
    Inventors: Laramie M. Gaster, Barry S. Orlek
  • Patent number: 4585588
    Abstract: Compounds of formula (I), ##STR1## or an N-oxide or pharmaceutically acceptable salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-7 alkyl, C.sub.3-7 cycloalkyl, C.sub.4-7 cycloalkenyl or C.sub.1-4 alkyl substituted by C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, C.sub.3-7 cycloalkyl, hydroxy, thiol, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, carboxy, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkanoyl, amino optionally substituted by one or two C.sub.1-4 alkyl or by C.sub.4-6 polymethylene optionally containing an oxygen or nitrogen atom, aminocarbonyl optionally N-substituted by one or two C.sub.1-4 alkyl, or benzoyl or phenyl either being optionally ring-substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or trifluoromethyl, R.sub.2 and R.sub.3 are the same or different and are hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halogen or trifluoromethyl, m is 1 to 3 and n is 1 or 2, the hydrogen atom bonded to the C.sub.a carbon atom being trans to the hydrogen atom bonded to the C.sub.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: April 29, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Laramie M. Gaster, Barry S. Orlek
  • Patent number: 4504480
    Abstract: Compounds of formula (I), ##STR1## or an N-oxide or pharmaceutically acceptable salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-7 alkyl, C.sub.3-7 cycloalkyl, C.sub.4-7 cycloalkenyl or C.sub.1-4 alkyl substituted by C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, C.sub.3-7 cycloalkyl, hydroxy, thiol, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, carboxy, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkanoyl, amino optionally substituted by one or two C.sub.1-4 alkyl or by C.sub.4-6 polymethylene optionally containing an oxygen or nitrogen atom, aminocarbonyl optionally N-substituted by one or two C.sub.1-4 alkyl, or benzoyl or phenyl either being optionally ring-substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or trifluoromethyl, R.sub.2 and R.sub.3 are the same or different and are hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alklthio, halogen or trifluoromethyl, m is 1 to 3 and n is 1 or 2, the hydrogen atom bonded to the C.sub.a carbon atom being trans to the hydrogen atom bonded to the C.sub.
    Type: Grant
    Filed: March 4, 1983
    Date of Patent: March 12, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Laramie M. Gaster, Barry S. Orlek
  • Patent number: RE35593
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sup.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 chloro, fluoro, bromo, cyclopropyl, C.sub.1-3 alkyl substituted by one, two or three halogen atoms, or R.sub.3 is a group (CH.sub.2).sub.n R.sub.9 where R.sub.9 is --CN, --OH, --OCH.sub.3, --SH, --SCH.sub.3, --C.tbd.CH or --CH.dbd.CH.sub.2 and n is O or 1, with the proviso that when n is 0, R.sub.9 is not --OH or --SH.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: August 19, 1997
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Steven M. Bromidge, Steven Dabbs