Patents Assigned to Mallinckrodt Specialty Chemicals Company
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Patent number: 5312970Abstract: D-propoxyphene can be prepared by reacting d-oxyphene and propionic anhydride. Preferably, an excess of propionic anhydride is used. The reaction easily proceeds at temperatures of 70.degree. to 80.degree. C. and produces yields exceeding 95 percent of theory. The free base d-propoxyphene can easily be converted in high yields to its hydrochloride or napsylate salts, both analgesics.Type: GrantFiled: March 19, 1992Date of Patent: May 17, 1994Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: John R. Duchek
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Patent number: 5312991Abstract: The compound p-aminophenol is prepared by catalytically hydrogenating nitrobenzene in an acidic reaction medium containing an amine of the formula (I) ##STR1## wherein R represents an alkyl group having from 6 to about 20 carbon atoms; R.sub.1 and R.sub.2 are the same or different, and are represented by the formula --[(CH.sub.2).sub.m O].sub.n H, wherein m is an integer of from 1 to about 5 and n is an integer of from 1 to about 10.Type: GrantFiled: June 9, 1992Date of Patent: May 17, 1994Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Douglas C. Miller
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Patent number: 5306507Abstract: A product and process for preparing a pharmaceutical composition for forming tablets, the composition containing pamabrom and pyrilamine maleate. In preferred embodiments, the composition also contains acetaminophen. A fluid bed granulator is charged with a first material containing pamabrom or pyrilamine maleate, and a first liquid containing pregelatinized starch is sprayed onto the first material so as to form a barrier coat. The barrier coated material is dried and then further coated with a second liquid containing only one of pamabrom and pyrilamine maleate, whichever was not present in the first material charged to the fluid bed granulator. The further coated material is then dried to a moisture content of from about 0.5% to less than about 2% by weight, so as to form particles in which the pamabrom and pyrilamine maleate are separated by the pregelatinized starch barrier.Type: GrantFiled: March 26, 1992Date of Patent: April 26, 1994Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Steven R. Freebersyser
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Patent number: 5284975Abstract: A method of preparing an .alpha.-d-phenylalkylbenzyl carbinol by the reaction of a phenylbenzyl ketone with an alkali metal enolate of an amide to form an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol, wherein the carbinol so produced possesses analgesic activity. In an embodiment of the invention, a phenylbenzyl ketone is reacted with an alkali metal enolate of an amide to form an aldol adduct, which is reacted with an alkali metal salt of a secondary amine to form a dianion; the dianion is alkylated with an alkyl halide to form an .alpha.-isomer of an aldol adduct, which is reduced and purified to form an .alpha.-d-phenylalkylbenzyl carbinol possessing analgesic activity.Type: GrantFiled: October 8, 1992Date of Patent: February 8, 1994Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Jacob Mathew
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Patent number: 5254776Abstract: Bromobiphenyls (such as 2-fluoro-4-bromobiphenyl) are synthesized by reacting together a phenylboronic acid (such as phenylboronic acid) and a bromoiodobenzene (such as 2-fluoro-4-bromoiodobenzene). The reaction generally takes place with the aid of a catalyst (such as palladium in a zero valance state) and an inert solvent (such as fluorobenzene). Control of temperature is very important to obtain both an acceptable reaction rate and an acceptable level of terphenyl byproduct.Type: GrantFiled: July 17, 1992Date of Patent: October 19, 1993Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: John F. Lang, Narayanasamy Gurusamy
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Patent number: 5227526Abstract: In a process for resolving 3-dimethylamino-2-methylpropiophenone (3-DAMP) material, a methanol solution containing a mixture of both 1- and d-enantiomers of 3-DAMP is formed. To this solution, ditoluyl-(L)-tartaric acid or ditoluyl-(D)-tartaric acid is added, so as to precipitate either the 1- or d-enantiomer of 3-DAMP as a salt. The precipitate then is isolated as a salt of a substantially pure enantiomer of 3-DAMP.Type: GrantFiled: June 16, 1992Date of Patent: July 13, 1993Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: John R. Duchek
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Patent number: 5200507Abstract: In solid phase peptide synthesis, resin-bound peptide is treated with hydrogen fluoride so as to cleave the peptide from the resin and form a first mixture of peptide, hydrogen fluoride and resin. The resin is removed from the first mixture so as to provide a resin-free second mixture including the polypeptide and the hydrogen fluoride. The polypeptide of the second mixture then is separated from the hydrogen fluoride.Type: GrantFiled: April 12, 1991Date of Patent: April 6, 1993Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Paul C. Chieng
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Patent number: 5164523Abstract: A fusion process for the rapid production of a granular metal soap passes a mixture of metal (e.g. zinc) oxide, one or more molten fatty acids and a catalyst through a heated reactor to form molten metallic soap which is then ejected through a spray nozzle in a cooling tower to form a granular soap product. Use of a spiral tubular reactor with a rapid heating coil is disclosed. The reaction is conducted under pressure to maintain water generated by the reaction in the liquid state. Flashing of the reaction water in the cooling tower aids in cooling and formation of fine granules.Type: GrantFiled: June 6, 1991Date of Patent: November 17, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Clyde R. Hudson, Edgar N. Nelson
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Patent number: 5162566Abstract: Substantially stereospacific (E)-tetrasubstituted acrylic esters, such as ##STR1## where R is hydrogen alkyl, R.sub.1 is alkyl, aryl or aralkyl, R.sub.2 and R.sub.4 are alkyl, are formed from racemic mixtures of corresponding unsaturated esters and cuprates of the formula (R.sub.3).sub.2 CuX, wherein R.sub.3 is alkyl, aryl or aralkyl, and X is lithium or magnesium halide.Type: GrantFiled: August 26, 1991Date of Patent: November 10, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Jacob Mathew
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Patent number: 5157169Abstract: In a process for producing a 3-halo-halobenzene or a 1-halo-3,5-dihalobenzene, a 2-halo-4-haloaniline or 2-halo-4,6-dihaloaniline is mixed with a deaminating agent. The 2-halo-4-haloaniline or 2-halo-4,6-dihaloaniline is deaminated so as to form a corresponding 3-halo-halobenzene or 1-halo-3,5-dihalobenzene.Type: GrantFiled: March 26, 1992Date of Patent: October 20, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Jerry R. Patton
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Patent number: 5149875Abstract: Aromatic amine compounds are halogenated in the presence of a quaternary ammonium halide.Type: GrantFiled: January 15, 1991Date of Patent: September 22, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Jerry R. Patton, Narayanasamy Gurusamy
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Patent number: 5138099Abstract: 4-fluorobenzaldehydes are formed from compounds of the formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different, and represent H, halogen, or an alkyl group of from 1 to about 10 carbon atoms, wherein, when at least one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is halogen, at least one of remaining R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is alkyl. the compound of formula of (I) is reacted with a formylating agent in the presence of FeCl.sub.3 in a reaction mixture, from which is separated a compound of the formula (II) ##STR2## wherein R.sub.1, R.sub.2 , R.sub.3 and R.sub.4 are as defined above.Type: GrantFiled: July 31, 1991Date of Patent: August 11, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: John F. Lang
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Patent number: 5132457Abstract: In a method for producing 2(R)-2-methyl-3-dimethylamino-propiophenone (d-DAMP), a chiral ester of the formula ##STR1## wherein R is an alkyl of from 1 to about 5 carbon atoms, is provided. The chiral easter of formula (I) is converted into a chiral amino-alcohol of the formula ##STR2## and the chiral amino-alcohol is oxidized so as to form d-DAMP.Type: GrantFiled: August 26, 1991Date of Patent: July 21, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Jacob Mathew
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Patent number: 5112975Abstract: 3,17-(diethoxycarbonyl)normorphine, which may be prepared by reaction of morphine with ethyl chloroformate, is converted to 3,17-(diethoxycarbonyl)normorphinone, a novel compound, by oxidation. The novel normorphinone derivative is converted to 3,17-(diethoxycarbonyl)normorphinone enol acetate, a second novel compound, by esterification with acetic anhydride or acetyl halide.A 14-hydroxy group is introduced into the novel dienol ester by oxidation with peracid. The resultant 14-hydroxy-3,17-(diethoxycarbonyl)normorphinone, a third novel compound, may be catalytically hydrogenated to produce 3,17-(diethoxycarbonyl)noroxymorphone. The latter intermediate may be converted to noroxymorphone by hydrolysis.Type: GrantFiled: September 14, 1989Date of Patent: May 12, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Rebecca A. Wallace
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Patent number: 5110367Abstract: A medical device is precision cleaned by being contacted with a choline-containing cleansing agent so as to remove pyrogens from the medical device.Type: GrantFiled: May 15, 1991Date of Patent: May 5, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: E. Wayne Ahlstrom
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Patent number: 5104648Abstract: A granular pharmaceutical composition containing 85 to 99 percent ibuprofen, 0.9 to 15.0 percent binder, and 0.1 to 5.0 percent polyvinylpyrrolidone, wherein the polyvinylpyrrolidone forms a film with a portion of said binder to form agglomerates, is disclosed. Ibuprofen may be fluidized with a portion of the binder in a fluid bed apparatus and sprayed with an aqueous dispersion of polyvinylpyrrolidone and the remainder of the binder. This granulation may be subsequently blended with additional excipients and, optionally, additional active pharmaceutical ingredients for direct compression into tablets.Type: GrantFiled: January 11, 1990Date of Patent: April 14, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Larry E. Denton, Anil M. Salpekar
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Patent number: 5055563Abstract: Disclosed is a process for continuous preparation of aromatic diazonium fluoride salts wherein diazotizable aromatic primary amines are continuously diazotized in a series of continuous-stirred tank reactors, wherein a portion of a premixed diazotization solution is cooled prior to being continuously fed into each of the reactors.Type: GrantFiled: June 13, 1990Date of Patent: October 8, 1991Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Bruce J. Lamb, Nickolas J. Stepaniuk
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Patent number: 5053542Abstract: A process for the production of 2,4-dihaloaniline, especially 4-bromo-2-fluoroaniline, via the halogenation (bromination) of 2-haloaniline (2-fluoroaniline) in the presence of quaternary ammonium halide (bromide) catalyst in an inert solvent. The yield and selectivity are very high and the inventive method includes continuous processing with recycle of the catalyst/solvent mixture.Type: GrantFiled: January 31, 1990Date of Patent: October 1, 1991Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Jerry R. Patton, Narayanasamy Gurusamy
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Patent number: 5052451Abstract: A dust control apparatus having a cover member lowerable into an opening of a container, the cover member having a radially expandable seal for sealing the opening, the cover member having a passage therethrough adapted to receive a conduit, the cover member being operable in telescoping relation to the conduit and the passage being sufficiently larger than the conduit for the passage of air between the cover member and conduit, the cover member being movable laterally relative to the conduit to enable the cover member to be lowered into a container which is not precisely aligned therewith, a filter sleeve having a lower end attached to the cover member and an upper end attached to the conduit, the filter sleeve being adapted to prevent the escape of dust from the space between the cover member and conduit, the filter sleeve being protected by the conduit from damage caused by materials flowing through the conduit, the apparatus including an optional fume collecting annulus locatable in surrounding relation tType: GrantFiled: February 26, 1991Date of Patent: October 1, 1991Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Michael J. Gentilcore, David G. Mock
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Patent number: 5041617Abstract: Multifunctional dithiodialkanoic acid esters useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by contacting a selected dithiodialkanoic acid chloride with a selected 4-(3-hydroxypropyl)(mono- or di-alkyl) phenol under ester-forming reaction conditions. In a preferred embodiment, the ester is bis-3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propyl dithiodipropionate.Type: GrantFiled: February 19, 1988Date of Patent: August 20, 1991Assignee: Mallinckrodt Specialty Chemicals CompanyInventors: Neil Dunski, Ali A. Bazzi, Henry J. Buehler