Patents Assigned to Sharps Associates
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Patent number: 4120873Abstract: 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: GrantFiled: July 8, 1977Date of Patent: October 17, 1978Assignee: Sharps AssociatesInventors: Cheuk Man Lee, Raymond John Michaels
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Patent number: 4096265Abstract: 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: GrantFiled: November 8, 1976Date of Patent: June 20, 1978Assignee: Sharps AssociatesInventors: Anil Chandra Ghosh, Raj Kumar Razdan
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Patent number: 4075132Abstract: The reaction of thebaine or dihydrothebaine-.phi. with potassium in liquid ammonia respectively in the absence or presence of catalyst yields .beta.-dihydrothebaine.Type: GrantFiled: December 23, 1976Date of Patent: February 21, 1978Assignee: Sharp AssociatesInventor: David Edward Portlock
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Patent number: 4051152Abstract: 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: GrantFiled: January 7, 1976Date of Patent: September 27, 1977Assignee: Sharps AssociatesInventors: Raj Kumar Razdan, Haldean Cloyce Dalzell, Patricia Herlihy
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Patent number: 4042694Abstract: 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: GrantFiled: March 8, 1976Date of Patent: August 16, 1977Assignee: Sharps AssociatesInventors: Louis Selig Harris, Harry George Pars, John Clark Sheehan, Raj Kumar Razdan
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Patent number: 4036857Abstract: 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: GrantFiled: February 2, 1976Date of Patent: July 19, 1977Assignee: Sharps AssociatesInventors: Raj Kumar Razdan, Haldean Cloyce Dalzell
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Patent number: 4025521Abstract: The reaction of thebaine or dihydrothebaine-.phi. with potassium in liquid ammonia respectively in the absence or presence of catalyst yields .beta.-dihydrothebaine.Type: GrantFiled: October 22, 1975Date of Patent: May 24, 1977Assignee: Sharps AssociatesInventor: David Edward Portlock
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Patent number: 4020163Abstract: 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: GrantFiled: July 10, 1975Date of Patent: April 26, 1977Assignee: Sharps AssociatesInventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan, Barbara Zitko Terris
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Patent number: 4007207Abstract: 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: GrantFiled: July 9, 1975Date of Patent: February 8, 1977Assignee: Sharps AssociatesInventors: Martin Winn, Raj Kumar Razdan, Haldean Cloyce Dalzell, Joyce Ruth Krei
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Patent number: 3992550Abstract: 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: GrantFiled: July 9, 1975Date of Patent: November 16, 1976Assignee: Sharps AssociatesInventors: Martin Winn, Raj Kumar Razdan, Haldean Cloyce Dalzell, Joyce Ruth Krei
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Patent number: 3991194Abstract: 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: GrantFiled: December 4, 1972Date of Patent: November 9, 1976Assignee: Sharps AssociatesInventors: Louis Selig Harris, Harry George Pars, John Clark Sheehan, Raj Kumar Razdan
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Patent number: 3987190Abstract: 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: GrantFiled: February 18, 1975Date of Patent: October 19, 1976Assignee: Sharps AssociatesInventors: Raj Kumar Razdan, Harry George Pars
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Patent number: 3972880Abstract: 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: GrantFiled: March 17, 1975Date of Patent: August 3, 1976Assignee: Sharps AssociatesInventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan
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Patent number: 3960871Abstract: 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: GrantFiled: March 5, 1974Date of Patent: June 1, 1976Assignee: Sharps AssociatesInventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan
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Patent number: 3951970Abstract: 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: GrantFiled: October 1, 1973Date of Patent: April 20, 1976Assignee: Sharps AssociatesInventors: Raj Kumar Razdan, Harry George Pars
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Patent number: 3946111Abstract: 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: GrantFiled: November 18, 1974Date of Patent: March 23, 1976Assignee: Sharps AssociatesInventors: Martin Winn, Raj Kumar Razdan, Haldean Cloyce Dalzell, Joyce Ruth Krei
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Patent number: 3941782Abstract: 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: GrantFiled: May 21, 1973Date of Patent: March 2, 1976Assignee: Sharps AssociatesInventors: Louis Selig Harris, Harry George Pars, Raj Kumar Razdan, John Clark Sheehan
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Patent number: 3934024Abstract: 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: GrantFiled: February 18, 1975Date of Patent: January 20, 1976Assignee: Sharps AssociatesInventors: Raj Kumar Razdan, Harry George Pars