Patents by Inventor Robin D. Clark
Robin D. Clark 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).
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Patent number: 5202333Abstract: The present invention is directed to 5-HT.sub.3 receptor antagonist compounds of formula I: ##STR1## in which the dashed line denotes an optional double bond;n is 1, 2 or 3;p is 0, 1, 2 or 3;q is 0, 1 or 2;each R.sup.1 is independently selected from halogen, hydroxy, lower alkoxy, lower alkyl, nitro, amino, amino carbonyl, (lower alkyl)amino, di(lower alkyl)amino, and (lower alkanoyl)amino;each R.sup.2 is lower alkyl; andR.sup.3 is a group selected from Formulae (a), (b), (c) and (d): ##STR2## in which u is 0 or 1;z is 1, 2 or 3; andR.sup.4 is C.sub.1-7 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-2 alkyl, or a group (CH.sub.2).sub.t R.sup.5 where t is 1 or 2 and R.sup.5 is thienyl, pyrrolyl, or furyl, each optionally further substituted by one or two substituents selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C.sub.Type: GrantFiled: May 22, 1991Date of Patent: April 13, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: Jacob Berger, Robin D. Clark, Richard M. Eglen, William L. Smith, Klaus K. Weinhardt
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Patent number: 5202318Abstract: Compounds of Formula I: ##STR1## in which Z is CH.sub.2 or C.dbd.O;X and Y are independently selected from hydrogen, halogen, hydroxy, lower alkoxy, lower alkyl, nitro, amino, aminocarbonyl, (lower alkyl)amino, di(lower alkyl)amino and (lower alkanoyl)amino; and R.sup.1 is a group selected from Formulae (a), (b), (c) (d) and (e): ##STR2## in which p is 0 or 1;n is 1, 2 or 3;R.sup.2 is hydrogen, lower alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.12 alkyl, or a group R.sup.6 -C.sub.1-2 alkyl in which R.sup.6 is thienyl, pyrrolyl or furyl optionally substituted by one or two substituents selected from lower alkyl, lower alkoxy, trifluoromethyl or halogen, or is phenyl optionally substituted by one or two substituents selected from C.sub.1-4 alkoxy, trifluoromethyl, halogen, nitro, carboxy, esterified carboxy, and C.sub.1-4 alkyl optionally further substituted by hydroxy, C.sub.1-4 alkoxy, carboxy, esterified carboxy or in vivo hydrolyzable acyloxy;each R.sup.Type: GrantFiled: May 28, 1991Date of Patent: April 13, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: Jacob Berger, Robin D. Clark, Richard M. Eglen, William L. Smith, Klaus K. Weinhardt
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Patent number: 5192770Abstract: .alpha.-Oxoacetamides of the formula R.sup.1 C(O)C(O)NR.sup.2 R.sup.3 in which R.sup.1 is optionally substituted phenyl, 1-indolyl, 2,3-dihydro-1-indolyl, 1-benzimidazolidinonyl, 3-benzofuranyl, 3-benzothiophenyl, 3-indolyl, and 1,2-alkano-3-indolyl; R.sup.2 is selected from: ##STR1## and R.sup.3 is selected from hydrogen or lower alkyl; and the pharmaceutically acceptable salts, individual isomers, mixtures of isomers, processes for preparation, compositions, and methods of use thereof.Type: GrantFiled: December 7, 1990Date of Patent: March 9, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, Richard M. Eglen, Joseph M. Muchowski, William L. Smith, Klaus K. Weinhardt
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Patent number: 5189041Abstract: 5-HT.sub.3 receptor antagonist compounds of the formula ##STR1## in which Z is --O--, --S-- or --N(R.sup.2)--; R.sup.1 and R.sup.2 are independently selected from hydrogen and lower alkyl or are together --(CH.sub.2).sub.n -- wherein n is 2 to 4; and R.sup.3 is selected from ##STR2## and the pharmaceutically acceptable salts, individual isomers, compositions, and methods of use thereof.Type: GrantFiled: November 16, 1990Date of Patent: February 23, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: Jacob Berger, Robin D. Clark
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Patent number: 4960891Abstract: The invention provides a process for preparing compounds, as a single enantiomer or mixture of enantiomers, represented by the formula: ##STR1## in which: X and Y are independently hydrogen, hydroxy, lower alkyl, lower alkoxy or halo, or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy, andZ is --SO.sub.2 R or --C(O)NR.sup.3 R.sup.4, in which;R is lower alkyl, optionally substituted phenyl, --(CH.sub.2).sub.m OR.sup.1 or --NR.sup.1 R.sup.2 wherein m is an integer of 1 to 6 and R.sup.1 and R.sup.2 are independently hydrogen or lower alkyl; andR.sup.3 and R.sup.4 are independently hydrogen, alkyl, optionally substituted phenyl or phenyl lower alkyl; orR.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached or R.sup.3 and R.sup.4 taken together with the nitrogen to which they are attached represent a heterocycle of the formula: ##STR2## wherein A is --CH.sub.2 --, --NR.sup.1 -- or oxygen; and novel intermediates.Type: GrantFiled: April 11, 1989Date of Patent: October 2, 1990Assignee: Syntex (U.S.A.) Inc.Inventor: Robin D. Clark
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Patent number: 4957914Abstract: 1,9-Alkano-bridged-2,3,4,5-tetrahydro-1H-3-benzazepines and the derivatives thereof, i.e., the compounds of Formula I: ##STR1## wherein: R is selected from the group consisting of: hydrogen, cyano, lower alkyl, lower alkenyl, and aralkyl;each of R.sup.1, R.sup.2 and R.sup.3 is independently selected from the group consisting of: hydrogen, hydroxy, halo, trifluoromethyl, nitro, amido, lower alkoxy, lower alkyl, and lower alkylthio; andY is lower alkylene having from two to four carbon atoms;and the pharmaceutically acceptable salts thereof, are useful as CNS agents, e.g., as antidepressants, anxiolytics and antihypertensives, and/or as precursors thereto.Type: GrantFiled: August 12, 1988Date of Patent: September 18, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, Jacob Berger, Klaus K. Weinhardt
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Patent number: 4956365Abstract: Compounds of formulas (1) and (2): ##STR1## in which: X and Y are independently hydrogen, hydroxy, lower alkyl, lower alkoxy or halo, or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy;W is oxygen or sulfur; andZ is --R.sup.1, --OR.sup.2 or --NR.sup.3 R.sup.4, whereinR.sup.1 is lower alkyl, lower haloalkyl, cycloalkyl, optionally substituted phenyl or phenyl lower alkyl, or heteroaryl;R.sup.2 is lower alkyl, optionally substituted phenyl or phenyl lower alkyl;R.sup.3 and R.sup.4 are independently hydrogen, alkyl, optionally substituted phenyl or phenyl lower alkyl; orR.sup.3 and R.sup.4 taken together with the nitrogen to which they are attached represent a heterocycle of the formula: ##STR2## wherein A is --(CH.sub.2).sub.m, --N(R.sup.5)-- or oxygen, in which m is an integer of 0-2 and R.sup.5 is hydrogen or lower alkyl;or a pharmaceutically acceptable salt thereof, are useful as .alpha..sub.2 -blockers.Type: GrantFiled: October 12, 1988Date of Patent: September 11, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, Andrew T. Kilpatrick, Michael Spedding
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Patent number: 4886798Abstract: Compounds of the formula (1): ##STR1## in which: X and Y are independently hydrogen, hydroxy, lower alkyl, lower alkoxy or halo, or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy, andR is lower alkyl, optionally substituted phenyl, --(CH.sub.2).sub.m OR.sup.1 or --NR.sup.1 R.sup.2, wherein m is an integer of 1 to 6 and R.sup.1 and R.sup.2 are independently hydrogen or lower alkyl, or --NR.sup.1 R.sup.2 taken together is a heterocycle of the formula: ##STR2## wherein A is --CH.sub.2 --, --NR.sup.1 -- or oxygen; or a pharmaceutically acceptable salt thereof, are useful as selective .alpha..sub.2 -blockers.Type: GrantFiled: March 29, 1988Date of Patent: December 12, 1989Assignee: Syntex (U.S.A.) Inc.Inventor: Robin D. Clark
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Patent number: 4847269Abstract: Intraocular hypertensive diseases such as glaucoma are treated with compounds represented by formula I ##STR1## or a pharmaceutically acceptable acid addition salt thereof, whereinR.sub.1 is alkyl of two to four carbon atoms; andR.sub.2 is alkyl of three or four carbon atoms; orR.sub.1 and R.sub.2 taken together with N form ##STR2## wherein n is 0, 1, or 2 and R.sub.5 and R.sub.6 are each independently lower alkyl or hydro;R.sub.3 is hydro or hydroxy;R.sub.4 is hydro, lower alkyl, amino, or lower alkylamino.Type: GrantFiled: August 22, 1986Date of Patent: July 11, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, L. David Waterbury
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Patent number: 4826869Abstract: N-(lower alkyl)-2-(3'-ureidobenzyl)pyrrolidines and N-(lower alkyl)-2-(3'-ureidobenzyl)-5-(lower alkyl)pyrrolidines are useful for lowering intraocular pressure in mammals, for example, in the treatment of glaucoma.Type: GrantFiled: February 19, 1988Date of Patent: May 2, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robin D. Clark, L. David Waterbury
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Patent number: 4791108Abstract: Compounds of formulas (1) and (2): ##STR1## in which: X and Y are independently hydrogen, hydroxy, lower alkyl, lower alkoxy or halo, or X and Y taken together is methylenendioxy or ethylene-1,2-dioxy, andR is lower alkyl, optionally substituted phenyl, --(CH.sub.2).sub.m OR.sup.1 or --NR.sup.1 R.sup.2 wherein m is an integer of 1 to 6 and R.sup.1 and R.sup.2 are independently hydrogen or lower alkyl, or --NR.sup.1 R.sup.2 taken together is a heterocycle of the formula: ##STR2## wherein A is --CH.sub.2 --, --NR.sup.1 -- or oxygen, or a pharmaceutically acceptable salt thereof, are useful as .alpha..sub.2 -blockers, especially as antidepressants.Type: GrantFiled: April 13, 1987Date of Patent: December 13, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Robin D. Clark
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Patent number: 4752621Abstract: Intraocular hypertensive diseases such as glaucoma are treated with compounds represented by formula I ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein R.sub.1 is alkyl of two to four carbon atoms;R.sub.2 is --(CH.sub.2).sub.n --C.sub.6 H.sub.4 --R.sub.5 ; wheren is an integer from 1 to 4; andR.sub.5 is --H, --OH, halo, lower alkyl, lower alkoxy, ureido, lower alkyl-ureido, lower alkyl-amido, or formamido;R.sub.3 is hydro or hydroxy; andR.sub.4 is hydro, lower alkyl, amino, or lower alkylamino.Type: GrantFiled: August 25, 1986Date of Patent: June 21, 1988Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, L. David Waterbury
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Patent number: 4672071Abstract: Compositions containing dihydropyridine derivatives which are useful for treating congestive heart failure, hypertension, or angina have the formula: ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein n is an integer from 0 to 8;Y is --O--, --NH--, --NR.sub.2 --, --S--, --S(O)--, --S(O).sub.2 --, or a bond;R.sub.1 and R.sub.2 are each independently A.sub.1, A.sub.2, A.sub.3 or A.sub.4 whereA.sub.1 is --(CH.sub.2).sub.m (CHOH).sub.p CH.sub.2 OH;A.sub.2 is --(CH.sub.2).sub.q CH.sub.(3-r) [(CH.sub.2).sub.s OH].sub.r ;A.sub.3 is --(CH.sub.2).sub.q CH.sub.(3-r) [(CH.sub.2).sub.p COOR.sub.3 ].sub.r ; andA.sub.4 is --(CH.sub.2).sub.m COOR.sub.3 ; wherem is an integer from 1 to 8;p is an integer from 0 to 4;q is an integer from 0 to 8;r is 2 or 3;s is an integer from 1 to 4; andR.sub.3 is H or alkyl of 1 to 18 carbon atoms;R.sub.4 is --NO.sub.2, --CF.sub.3, or halo; andR.sub.5 is lower alkyl or --CH.sub.2 CH.sub.2 OCH.sub.3.Type: GrantFiled: December 12, 1985Date of Patent: June 9, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, Moysey M. Povzhitkov
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Patent number: 4642378Abstract: Intraocular hypertensive diseases such as glaucoma are treated with compounds represented by formula I ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein R.sub.1 is alkyl of two to four carbon atoms;R.sub.2 is --(CH.sub.2).sub.n --C.sub.6 H.sub.4 --R.sub.5 ; wheren is an integer from 1 to 4; andR.sub.5 is --H, --OH, halo, lower alkyl, lower alkoxy, ureido, lower alkyl-ureido, lower alkyl-amido, or formamido;R.sub.3 is hydro or hydroxy; andR.sub.4 is hydro, lower alkyl, amino, or lower alkylamino.Type: GrantFiled: April 11, 1985Date of Patent: February 10, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, L. David Waterbury
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Patent number: 4629730Abstract: Elevated intraocular pressure diseases such as glaucoma are treated with compounds represented by formula I ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein R.sub.1 is alkyl of two to four carbon atoms; andR.sub.2 is alkyl of three or four carbon atoms; orR.sub.1 and R.sub.2 taken together with N form ##STR2## wherein n is 0, 1, or 2 and R.sub.5 and R.sub.6 are each independently lower alkyl or hydro;R.sub.3 is hydro or hydroxy;R.sub.4 is hydro, lower alkyl, amino, or lower alkylamino.Type: GrantFiled: April 11, 1985Date of Patent: December 16, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Robin D. Clark, L. David Waterbury
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Patent number: 4567264Abstract: Novel compounds of the general formula ##STR1## and the pharmaceutically acceptable esters and acid addition salts thereof, wherein:R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each independently hydrogen, lower alkyl, lower alkoxy, cyano, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl, N-optionally substituted alkylamido, except that when R.sup.1 is methyl, R.sup.4 is not methyl; orR.sup.2 and R.sup.3 together form --OCH.sub.2 O--;R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are each independently hydrogen, lower acyl, aminocarbonylmethyl, cyano, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl, di-lower alkyl amino; orR.sup.6 and R.sup.7 together form --CH.dbd.CH--CH.dbd.CH--;R.sup.7 and R.sup.8 together form --OCH.sub.2 O--;R.sup.11 and R.sup.12 are each independently hydrogen or lower alkyl; andW is oxygen or sulfur.Type: GrantFiled: May 18, 1983Date of Patent: January 28, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Robin D. Clark, Arthur M. Strosberg, Jean-Claude G. Pascal, Roger Whiting
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Patent number: 4558129Abstract: Novel compounds of the general formula: ##STR1## and the pharmaceutically acceptable esters and acid addition salts thereof, wherein:R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl; orR.sup.2 and R.sup.3 together form --OCH.sub.2 O--; andR.sup.10 and R.sup.11 are each independently hydrogen or lower alkyl.These compounds combine .beta.-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including hypertension, arrhythmias and variant and exercise induced angina.Type: GrantFiled: May 18, 1983Date of Patent: December 10, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Robin D. Clark, Arthur M. Strosberg
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Patent number: 4542027Abstract: A compound represented by the formula ##STR1## wherein R.sup.1 is an alkali metal cation or hydrogen and which useful for increasing the feed efficiency of ruminants and for treating coccidiosis in domestic animals, especially chickens.Type: GrantFiled: February 23, 1984Date of Patent: September 17, 1985Assignee: Syntex (U.S.A.) Inc.Inventor: Robin D. Clark
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Patent number: 4499100Abstract: Novel compounds of the general formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl or lower alkyl sulfonyl;R.sup.5 is hydrogen or lower alkyl;m is 0 or 1;W is alkylene, --CH.dbd.CH--, --O--, or --N(R.sup.6)--, where R.sup.6 is lower alkyl or hydrogen;n is 0 or 1; andQ is lower alkyl, cycloalkyl or optionally substituted phenyl.These compounds combine .beta.-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including myocardial infarction, hypertension, arrhythmia and variant and exercise induced angina. The compounds are also useful in immunosuppressant therapy for immune diseases, such as rheumatoid arthritis.Type: GrantFiled: May 18, 1983Date of Patent: February 12, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Robin D. Clark
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Patent number: 4431665Abstract: Compounds represented by the formula ##STR1## wherein R.sup.1 is an aliphatic or alicyclic hydrocarbon acyl group of two to eighteen carbon atoms and R.sup.2 is an alkali metal cation or hydrogen are useful for increasing the feed efficiency of ruminants and for treating coccidiosis in domestic animals, especially chickens.Type: GrantFiled: June 24, 1980Date of Patent: February 14, 1984Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Robin D. Clark