Patents by Inventor William F. Michne
William F. Michne 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: 6218538Abstract: There are provided novel compounds of formula (I) including their 3,4-dihydropyrimidine tautomer form, wherein R1, R2, R3, R4, R5, X and n are as defined in the specification, and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy. The compounds are antagonists of N-type neuronal calcium channels useful in the treatment of cerebrovascular ischaemia and pain.Type: GrantFiled: October 14, 1998Date of Patent: April 17, 2001Assignee: Astra AktiebolagInventors: Eileen S. Downs, William F. Michne, M. Edward Pierson, Jr.
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Patent number: 6057332Abstract: There are provided novel compounds of formula (I) ##STR1## including their 3,4-dihydropyrimidine tautomer form, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X and n are as defined in the specification, and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy. The compounds are antagonists of N-type neuronal calcium channels useful in the treatment of cerebrovascular ischaemia and pain.Type: GrantFiled: October 14, 1998Date of Patent: May 2, 2000Assignee: Astra AktiebolagInventors: William F. Michne, M. Edward Pierson, Jr.
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Patent number: 5364867Abstract: 4-Phenylpiperidines of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxy or lower-alkoxy;R.sub.2 is hydrogen, hydroxy, lower-alkanoyl, aroyl, lower-alkoxycarbonyl, lower-alkanoyloxy, lower-alkoxycarbonyl, or CONR.sub.3 R.sub.4 ; R.sub.3 and R.sub.4 are the same or different lower-alkyl or R.sub.3 and R.sub.4 together represent a lower-alkylene chain;X is methylene or carbonyl;Y is methylene, C.dbd.NOH, hydroxymethylene or carbonyl;or pharmaceutically acceptable acid addition salts thereof, are useful in the treatment of psychoses and other ailments of the central nervous system.Type: GrantFiled: November 30, 1992Date of Patent: November 15, 1994Assignee: Sterling Winthrop Inc.Inventors: Diane L. DeHaven-Hudkins, John P. Mallamo, William F. Michne
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Patent number: 5314894Abstract: (S)-(+)-Hydroxychloroquine substantially free of (R)-(-)-hydroxychloroquine, or a pharmaceutically acceptable acid-addition salt thereof and a method of use thereof and a composition containing it for the treatment of malaria, lupus erythematosus or rheumatoid arthritis.Type: GrantFiled: September 15, 1992Date of Patent: May 24, 1994Assignee: Sterling Winthrop Inc.Inventors: Vera J. Stecher, William F. Michne
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Patent number: 5290789Abstract: The invention is related to compounds, being useful in treating psychosis, of the formula: ##STR1## wherein: R.sup.1 is hydrogen, lower-alkyl or phenyl-lower-alkyl;R.sup.2 and R.sup.4 are the same or different lower-alkyl;R.sup.3 is hydrogen or lower-alkyl;m is two or three;n is an integer from zero to three; andR.sup.5 is hydrogen, lower-alkyl, C.sub.3 -C.sub.7 -monocyclic cycloalkyl, allyl, or propargyl;or a pharmaceutically acceptable acid-addition salt thereof.Type: GrantFiled: November 20, 1992Date of Patent: March 1, 1994Assignee: Sterling Wintrop Inc.Inventors: Diane L. DeHaven-Hudkins, John P. Mallamo, William F. Michne, Martha R. Heimann
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Patent number: 5290796Abstract: The invention is related to compounds, being useful in treating psychosis, of the formula: ##STR1## wherein R.sup.1 is lower-alkyl, or phenyl-lower-alkyl;R.sup.2, R.sup.3 and R.sup.4 are the same or different lower-alkyl;n is zero or one;R.sup.5 is hydrogen, lower-alkyl, C.sub.3 -C.sub.7 -monocyclic cycloalkyl, lower-alkoxy, phenyl, phenyl-lower-alkyl, phenyl-lower-alkyl in which the phenyl ring is substituted in the 2, 3, or 4-position by one to two, the same or different, halogen substituents, or R.sup.5 is a 5-membered aromatic monocyclic heterocycle selected from the group consisting of thienyl, furanyl and isoxazolyl;R.sup.6 is hydrogen or lower-alkyl; or when n is zero, R.sup.5 and R.sup.6 together are --(CH.sub.2).sub.m -- wherein m is an integer from four to six; with the proviso that when R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl, n is zero and R.sup.6 is hydrogen or methyl, R.sup.5 cannot be hydrogen; further provided that when n is zero, R.sup.Type: GrantFiled: November 20, 1992Date of Patent: March 1, 1994Assignee: Sterling Winthrop Inc.Inventors: Diane L. DeHaven-Hudkins, John P. Mallamo, William F. Michne, Martha R. Heimann
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Patent number: 5286733Abstract: The invention is related to compounds, being useful in treating psychosis, of the formula: ##STR1## wherein: R.sup.1 is hydrogen, lower-alkyl, phenyl-lower-alkyl, C.sub.3 -C.sub.7 -monocyclic cycloalkyl-lower-alkyl, or hydroxy-C.sub.3 -C.sub.7 -monocycliccycloalkyl-lower-alkyl;R.sup.2 is lower-alkyl;R.sup.3 is hydrogen or lower-alkyl;R.sup.4 is lower-alkyl;n is an integer from zero to three; andR.sup.5 is hydroxy, lower-alkoxy, lower-alkyl, C.sub.3 -C.sub.7 -monocyclic cycloalkyl, phenyl, or a 5-membered heterocycle selected from furanyl, thienyl and isoxazolyl;with the proviso that when n is zero, R.sup.5 is other than hydroxy or a pharmaceutically acceptable acid-addition salt thereof.Type: GrantFiled: November 20, 1992Date of Patent: February 15, 1994Assignee: Sterling Winthrop Inc.Inventors: Diane L. DeHaven-Hudkins, John P. Mallamo, William F. Michne, Martha R. Heimann
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Patent number: 5240935Abstract: Novel substituted 2-azabicyclo[2.2.2]octane derivatives, pharmaceutical compositions containing them, methods for treating central nervous system disorders utilizing them, and processes for synthesizing them.Type: GrantFiled: November 20, 1992Date of Patent: August 31, 1993Assignee: Sterling Winthrop Inc.Inventors: Diane L. DeHaven-Hudkins, John P. Mallamo, William F. Michne, Martha R. Heimann
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Patent number: 5239110Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is lower-alkanoyl or hydrogen;R.sub.2 and R.sub.3 are the same or different lower-alkyl; or pharmaceutically acceptable acid-addition salts thereof are useful in the treatment of disorders of the central nervous system.Type: GrantFiled: December 30, 1992Date of Patent: August 24, 1993Assignee: Sterling Winthrop, Inc.Inventors: John P. Mallamo, William F. Michne, Aram Mooradian
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Patent number: 4335243Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.Type: GrantFiled: March 12, 1981Date of Patent: June 15, 1982Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4296238Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.Type: GrantFiled: May 7, 1980Date of Patent: October 20, 1981Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4255579Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.Type: GrantFiled: February 5, 1979Date of Patent: March 10, 1981Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4239890Abstract: 1-R.sub.1 -2-Q-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -1,2,3,4,4a,5,10,10a-Octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2.2.2]oct-5-ene.Type: GrantFiled: February 5, 1979Date of Patent: December 16, 1980Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Intermediates for 11-[3-oxo-.omega.(2- and 3-furyl)-lower-alkyl]hexahydro-2,6-methano-3-benzazocines
Patent number: 4228286Abstract: 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -11(eq)-[CH.sub.2 CH.sub.2 CO(CH.sub.2).sub.n -(2- and 3-furyl)]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared either by heating, with formic acid in an organic solvent or with certain ammonium formates, certain lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 "'-3-[CO(CH.sub.2).sub.n -(2- and 3-furyl)]-1,2,3,4,4 a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylates or by reaction of a lower-alkyl .beta.-[3-R.sub.1 -6-(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionate with 2 or 3-furylacetic acid in the presence of a strong base.Type: GrantFiled: August 30, 1979Date of Patent: October 14, 1980Assignee: Sterling Drug Inc.Inventors: Thomas R. Lewis, William F. Michne -
Patent number: 4214085Abstract: 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '''-11(ax)-R.sub.3 -11(eq)-[CH.sub.2 CH.sub.2 CO(CH.sub.2).sub.n -(2- and 3-furyl)]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared either by heating, with formic acid in an organic solvent or with certain ammonium formates, certain lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '''-3-[CO(CH.sub.2).sub.n -(2- and 3-furyl]-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carb oxylates or by reaction of a lower-alkyl .beta.-[3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '''-11(ax)-R.sub.3 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionate with 2- or 3-furylacetic acid in the presence of a strong base.Type: GrantFiled: May 4, 1979Date of Patent: July 22, 1980Assignee: Sterling Drug Inc.Inventors: Thomas R. Lewis, William F. Michne
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Patent number: 4208523Abstract: 3-R.sub.1 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -6(eq)-R.sub.4 -11(eq)-(CH.sub.2 CH.sub.2 CH.sub.2 R.sub.5)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, generally useful as morphine-like analgesics and as narcotic antagonists, are prepared by reducing, under Wolff-Kishner reaction conditions, a corresponding 3-R.sub.1 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -6(eq)-R.sub.4 -11(eq)-(CH.sub.2 CH.sub.2 COR.sub.5)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine and, if desired, cleaving a lower-alkoxy, methoxymethoxy or benzyloxy group to an hydroxy group.Type: GrantFiled: November 30, 1978Date of Patent: June 17, 1980Assignee: Sterling Drug Inc.Inventors: William F. Michne, Thomas R. Lewis
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Patent number: 4202983Abstract: 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -11(eq)-[CH.sub.2 CH.sub.2 CO(CH.sub.2).sub.n -X-Alk]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics, are prepared by heating, with formic acid in an organic solvent or with certain ammonium formates, a lower-alkyl 1-R.sub.1 -3-[Alk-X-(CH.sub.2).sub.n -CO]-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 "'-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylat e.Type: GrantFiled: March 26, 1979Date of Patent: May 13, 1980Assignee: Sterling Drug Inc.Inventors: Thomas R. Lewis, William F. Michne
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Patent number: 4202984Abstract: .beta.-[3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '"-11(ax)-R.sub.3 -1,2,3,4,5,6,-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionic acids, esters and amides, useful as analgesics and narcotic antagonists, are prepared by heating, with formic acid in an organic solvent or with certain ammonium formates, certain di-lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 "'-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3,3-dicarbox ylates, to prepare the esters, hydrolysis of the latter to prepare the acids and conversion of the acids to a mixed anhydride and reaction of the latter with ammonia or an appropriate amine to form the amides.Type: GrantFiled: May 4, 1979Date of Patent: May 13, 1980Assignee: Sterling Drug Inc.Inventors: Thomas R. Lewis, William F. Michne
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Patent number: 4180667Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, and 1-R.sub.1 -2-Q-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -1,2,3,4,4a,5,10,10a-octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2.2.2]-oct-5-ene.Type: GrantFiled: February 13, 1978Date of Patent: December 25, 1979Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4148794Abstract: Lower-alkyl 1-R.sub.1 -3-R.sub.5 CO-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '"-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylat es, useful as intermediates for the preparation of 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '"-11(ax)-R.sub.3 -11(eq)-CH.sub.2 CH.sub.2 COR.sub.5 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared by acylation of an appropriate lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.C-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '"-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylat e or carboxylation of an appropriate 1-R.sub.1 -3-COR.sub.5 "-4.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '"-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline.Type: GrantFiled: February 16, 1978Date of Patent: April 10, 1979Assignee: Sterling Drug Inc.Inventors: Thomas R. Lewis, William F. Michne