Patents Assigned to Sharps Associates
  • Patent number: 4120873
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is methyl or R.sub.1 R.sub.1 is oxygen; R.sub.2 is alkyl or halogen substituted phenyl alkyl; and R.sub.3 is hydrogen, loweralkyl, loweralkenyl or loweralkynyl.
    Type: Grant
    Filed: July 8, 1977
    Date of Patent: October 17, 1978
    Assignee: Sharps Associates
    Inventors: Cheuk Man Lee, Raymond John Michaels
  • Patent number: 4096265
    Abstract: Benzopyrano[3,4-d]pyridine-2-cyano, carboxamidoximes and carboximidates of the formula ##STR1## wherein R represents -C.ident.N, ##STR2## R.sub.1 is a lower alkyl, R.sub.2 is hydrogen or a lower alkyl and R.sub.3 is a straight or branched alkyl having 1 to 20 carbons, a cycloalkyl-lower alkyl group in which the cycloalkyl group has 3 to 8 carbons or it is an arylalkyl group, and R.sub.4 is a lower alkyl group.The compounds are useful for lowering blood pressure.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: June 20, 1978
    Assignee: Sharps Associates
    Inventors: Anil Chandra Ghosh, Raj Kumar Razdan
  • Patent number: 4075132
    Abstract: The reaction of thebaine or dihydrothebaine-.phi. with potassium in liquid ammonia respectively in the absence or presence of catalyst yields .beta.-dihydrothebaine.
    Type: Grant
    Filed: December 23, 1976
    Date of Patent: February 21, 1978
    Assignee: Sharp Associates
    Inventor: David Edward Portlock
  • Patent number: 4051152
    Abstract: Benzopyrans of the formula ##STR1## wherein n represents 0 or 1, R is an alkyl group having 1 to 20 carbon atoms, an aryl-lower alkyl group or a cycloalkyl-lower alkyl group, R.sub.1 is hydrogen or ##STR2## wherein R.sub.4 is lower alkyl, phenyl, cycloalkyl-lower alkyl or aryl-lower alkyl, R.sub.2 is a lower alkyl and R.sub.3 is hydrogen or one or two lower alkyl groups, pharmaceutical compositions containing the compounds, and uses of the compounds as tranquilizers and analgesics.
    Type: Grant
    Filed: January 7, 1976
    Date of Patent: September 27, 1977
    Assignee: Sharps Associates
    Inventors: Raj Kumar Razdan, Haldean Cloyce Dalzell, Patricia Herlihy
  • Patent number: 4042694
    Abstract: Novel heterocyclic esters of benzopyranopyridines represented by the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, lower alkanoyl, cycloalkyl-lower alkyl, cycloalkyl-lower alkanoyl, lower alkenyl, lower alkynyl, halo-loweralkenyl, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl; R.sub.2 is lower alkyl; R.sub.3 is an alkyl having one to twenty carbon atoms or a cycloalkyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R.sub.4 is a group of the formula ##STR2## a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH.sub.2, O, S or N--R.sub.5 with R.sub.5 being hydrogen or lower alkyl, with the limitation that when X is O, S or N--R.sub.5, a and b each must be 2 and R.sub.6 is hydrogen or a lower alkyl group bonded to a carbon in the ring; and the acid addition salts thereof.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: August 16, 1977
    Assignee: Sharps Associates
    Inventors: Louis Selig Harris, Harry George Pars, John Clark Sheehan, Raj Kumar Razdan
  • Patent number: 4036857
    Abstract: 3-Formyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol, ethers and esters thereof having the formula ##STR1## wherein R is hydrogen, lower alkyl or lower alkanoyl and R.sub.6 is formyl or 1,3-dithiolan-2-yl but is 1,3-dithiolan-2-yl only when R is hydrogen, and derivatives thereof of the formula ##STR2## wherein R.sub.1 is hydrogen or lower alkanoyl, R.sub.2 is alkyl, aryl-lower alkyl or cycloalkyl-lower alkyl, A represents ##STR3## when R.sub.1 is hydrogen and R.sub.3 is lower alkyl, and A is ##STR4## when R.sub.1 is lower alkanoyl and R.sub.4 is the same lower alkanoyl represented by R.sub.1, processes of making such compounds and intermediates useful in such processes, pharmaceutical compositions containing the compounds and the use of the compounds as tranquilizing and antidepressant agents.
    Type: Grant
    Filed: February 2, 1976
    Date of Patent: July 19, 1977
    Assignee: Sharps Associates
    Inventors: Raj Kumar Razdan, Haldean Cloyce Dalzell
  • Patent number: 4025521
    Abstract: The reaction of thebaine or dihydrothebaine-.phi. with potassium in liquid ammonia respectively in the absence or presence of catalyst yields .beta.-dihydrothebaine.
    Type: Grant
    Filed: October 22, 1975
    Date of Patent: May 24, 1977
    Assignee: Sharps Associates
    Inventor: David Edward Portlock
  • Patent number: 4020163
    Abstract: Heterocyclic esters of 1,4-ethano-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-b]pyridines and 1,4-ethano-1,2,3,4,13,14-hexahydro-5H-[1]benzopyrano[3,4-b]pyridines. The esters have the formulas ##STR1## wherein R.sub.2 is lower alkyl, R.sub.3 is an alkyl having one to twenty carbon atoms, a cycloalkyl-lower alkyl or a phenyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R.sub.4 is a group of the formula ##STR2## wherein a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH.sub.2, O, S or N--R.sub.5 with R.sub.5 being hydrogen or lower alkyl, and R.sub.6 is hydrogen or a lower alkyl group bonded to a carbon in the ring.The compounds have pharmacological activity, including analgesic, anti-convulsive and tranquilizing activity in animals. The compounds can be administered in pharmaceutical composition form.
    Type: Grant
    Filed: July 10, 1975
    Date of Patent: April 26, 1977
    Assignee: Sharps Associates
    Inventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan, Barbara Zitko Terris
  • Patent number: 4007207
    Abstract: 1,2,3,4-Tetrahydrocyclopenta[c][1]benzopyrans of the formulae ##STR1## wherein R is a lower alkyl group having 1 to 5 carbons, R.sub.1 is hydrogen or a lower alkyl group having 1 to 5 carbons, R.sub.2 is a lower alkyl group and R.sub.3 is an alkyl group having 1 to 20 carbon atoms, a phenyl-lower alkyl group or a cycloalkyl-lower alkyl group. The compounds have anti-hypertensive, antidepressant, analgesic, anticonvulsant, anti-anxiety, sedative-hypnotic and tranquilizing activity in animals.
    Type: Grant
    Filed: July 9, 1975
    Date of Patent: February 8, 1977
    Assignee: Sharps Associates
    Inventors: Martin Winn, Raj Kumar Razdan, Haldean Cloyce Dalzell, Joyce Ruth Krei
  • Patent number: 3992550
    Abstract: 1,2,3,4-Tetrahydrocyclopenta[c] [1]benzopyrans of the formulae ##SPC1##Wherein R is a lower alkyl group having 1 to 5 carbons, R.sub.1 is hydrogen or a lower alkyl group having 1 to 5 carbons, R.sub.2 is a lower alkyl group and R.sub.3 is an alkyl group having 1 to 20 carbon atoms, a phenyl-lower alkyl group or a cycloalkyl-lower alkyl group. The compounds have anti-hypertensive, antidepressant, analgesic, anticonvulsant, anti-anxiety and tranquilizing activity in animals.
    Type: Grant
    Filed: July 9, 1975
    Date of Patent: November 16, 1976
    Assignee: Sharps Associates
    Inventors: Martin Winn, Raj Kumar Razdan, Haldean Cloyce Dalzell, Joyce Ruth Krei
  • Patent number: 3991194
    Abstract: Novel heterocyclic esters of benzopyranopyridines represented by the formula ##SPC1##Wherein R.sub.1 is hydrogen, lower alkyl, lower alkanoyl, cycloalkyl-lower alkyl, cycloalkyl-lower alkanoyl, lower alkenyl, lower alkynyl, halo-loweralkenyl, phenyl-lower alkyl, phenyl-lower alkenyl or phenyl-lower alkynyl; R.sub.2 is lower alkyl; R.sub.3 is an alkyl having one to twenty carbon atoms or a cycloalkyl-lower alkyl, Y is a straight or branched chain alkylene having one to eight carbon atoms, and R.sub.4 is a group of the formula ##EQU1## a is an integer from 1 to 4, b is an integer from 1 to 4 and X is CH.sub.2, O, S or N--R.sub.5 with R.sub.5 being hydrogen or lower alkyl, with the limitation that when X is O, S or N--R.sub.5, a and b each must be 2 and R.sub.6 is hydrogen or a lower alkyl group bonded to a carbon in the ring; and the acid addition salts thereof.
    Type: Grant
    Filed: December 4, 1972
    Date of Patent: November 9, 1976
    Assignee: Sharps Associates
    Inventors: Louis Selig Harris, Harry George Pars, John Clark Sheehan, Raj Kumar Razdan
  • Patent number: 3987190
    Abstract: A method of reducing blood pressure in a hypertensive mammalian patient by administering 1,2-dihydro-4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1 ]benzopyran or 1,2-dihydro-5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-3H,5H-thiopyrano- 8 2,3-c][1]benzopyran. Pharmaceutical compositions containing 1,2-dihydro-4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1 ]benzopyran or 1,2-dihydro-5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-3H,5H-thiopyrano[ 2,3-c][1]benzopyran dispersed in a pharmaceutical carrier.
    Type: Grant
    Filed: February 18, 1975
    Date of Patent: October 19, 1976
    Assignee: Sharps Associates
    Inventors: Raj Kumar Razdan, Harry George Pars
  • Patent number: 3972880
    Abstract: Novel thienobenzopyran and thiopyranobenzopyran esters represented by the formula ##SPC1##Wherein n is 0 to 3 and m is 0 to 3 and m + n = 2 or 3, R.sub.1 is lower alkyl, R.sub.2 is alkyl or cycloalkyl-lower alkyl, R.sub.4 is hydrogen or lower alkyl, R.sub.5 is hydrogen or lower alkyl, and R.sub.3 is ##EQU1## wherein Y is a straight or branched chain C.sub.1 to C.sub.8 alkylene, R.sub.6 is hydrogen or a lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, X is CH.sub.2, O, S or NR.sub.7 wherein R.sub.7 is hydrogen or lower alkyl, with the limitation that when X is O, S or NR.sub.7, a and b each must be 2; and the acid addition salts thereof.
    Type: Grant
    Filed: March 17, 1975
    Date of Patent: August 3, 1976
    Assignee: Sharps Associates
    Inventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan
  • Patent number: 3960871
    Abstract: Novel thienobenzopyran and thiopyranobenzopyran esters represented by the formula ##SPC1##Wherein n is 0 to 3 and m is 0 to 3 and m + n = 2 or 3, R.sub.1 is lower alkyl, R.sub.2 is alkyl or cycloalkyl-lower alkyl, R.sub.4 is hydrogen or lower alkyl, R.sub.5 is hydrogen or lower alkyl, and R.sub.3 is ##EQU1## wherein Y is a straight or branched chain C.sub.1 to C.sub.8 alkylene, R.sub.6 is hydrogen or a lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, X is CH.sub.2, O, S or NR.sub.7 wherein R.sub.7 is hydrogen or lower alkyl, with the limitation that when X is O, S or NR.sub.7, a and b each must be 2; and the acid addition salts thereof.
    Type: Grant
    Filed: March 5, 1974
    Date of Patent: June 1, 1976
    Assignee: Sharps Associates
    Inventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan
  • Patent number: 3951970
    Abstract: Compounds of the formula ##SPC1##And acid addition salts thereof, wherein R represents an alkyl group having 1 to 20 carbon atoms, an arylalkyl group, or a cycloalkyl-lower alkyl group, R.sub.1 and R.sub.2 represent hydrogen or the same or different lower alkyl or lower alkanoyl groups; and Z represents --NH.sub.2, --NHR.sub.3, --NR.sub.3 R.sub.4, or ##EQU1## WHERE R.sub.3 is lower alkyl, or phenyl-lower alkyl, R.sub.4 is lower alkyl or phenyl-lower alkyl, m is an integer from 0 to 6, n is an integer from 0 to 6, m + n is an integer from 3 to 6, and X is CH.sub.2, CHR.sub.3, O, S, or NR.sub.3.The compounds have pharmacological activity, including antidepressant and anti-hypertensive activity, in animals.
    Type: Grant
    Filed: October 1, 1973
    Date of Patent: April 20, 1976
    Assignee: Sharps Associates
    Inventors: Raj Kumar Razdan, Harry George Pars
  • Patent number: 3946111
    Abstract: 1,2-Dihydro-4H-thieno-[2,3-c][1]benzopyrans of the formulae ##SPC1##Wherein R is a lower alkyl group having 1 to 5 carbons, R.sub.1 is hydrogen or a lower alkyl group having 1 to 5 carbons, R.sub.2 is a lower alkyl group and R.sub.3 is an alkyl group having 1 to 20 carbon atoms, a phenyl-lower alkyl group or a cycloalkyl-lower alkyl group. The compounds have analgesic, antihypertensive, antidepressant, anticonvulsant, antianxiety, sedative-hypnotic and/or tranquilization activity.
    Type: Grant
    Filed: November 18, 1974
    Date of Patent: March 23, 1976
    Assignee: Sharps Associates
    Inventors: Martin Winn, Raj Kumar Razdan, Haldean Cloyce Dalzell, Joyce Ruth Krei
  • Patent number: 3941782
    Abstract: This invention relates to novel esters of benzopyrans represented by the formulae ##SPC1##Wherein R and R' are hydrogen or C.sub.1 -C.sub.6 alkyl and when alkyl are on the same or different carbons; R.sub.1 is C.sub.1 -C.sub.6 alkyl; R.sub.2 is C.sub.1 -C.sub.20 alkyl, lowercycloalkyloweralkyl or lowercycloalkyl; n is an integer from 3 to 7, and particularly 3 to 5; Y is a straight or branched chain C.sub.1 -C.sub.8 alkylene; and R.sub.3 is ##EQU1## WHEREIN A IS AN INTEGER FROM 1 TO 4, B IS AN INTEGER FROM 1 TO 4, X is O,S, CH.sub.2 or NR.sub.4 and R.sub.4 is hydrogen C.sub.1 -C.sub.6 alkyl, and R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl; and the acid addition salts thereof. The compounds exhibit analgesic and central nervous system activity.
    Type: Grant
    Filed: May 21, 1973
    Date of Patent: March 2, 1976
    Assignee: Sharps Associates
    Inventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan
  • Patent number: 3934024
    Abstract: A method of relieving pain in a mammalian patient suffering therefrom by administering 1,2-dihydro-5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-3H,5H-thiopyrano[ 2,3-c][1]benzopyran.
    Type: Grant
    Filed: February 18, 1975
    Date of Patent: January 20, 1976
    Assignee: Sharps Associates
    Inventors: Raj Kumar Razdan, Harry George Pars