Patents Assigned to Syntex Corporation
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Patent number: 3989731Abstract: Production of dimers of dicyclopentadienyl iron compounds by the reaction of a dicyclopentadienyl iron compound and a coupling agent in the presence of an acid catalyst in an organic solvent. The process involves a two-phase system wherein one phase comprises said coupling agent, a strong acid, and a polar organic solvent; and the second phase comprises said iron compound which is slightly soluble in the first phase. Dimers of dicyclopentadienyl iron compounds are excellent anti-oxidants and are also useful in controlling the rate of combustion of solid combustion mixtures.Type: GrantFiled: September 13, 1968Date of Patent: November 2, 1976Assignee: Syntex CorporationInventor: Meldon L. Talbot
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Patent number: 3988365Abstract: Resolution of mixtures of d and 1,2-(6-methoxy-2-napthyl)propionic acid with cinchonidine to yield the d-isomer is conducted by using, in combination with the cinchonidine, an inorganic base having a basicity, pKa, greater than 8 and forming a salt of 2-(6-methoxy-2-napthyl)propionic acid more soluble than the solubility of the corresponding cinchonidine salts. After the cinchonidine salt product is cleaved by treatment with a strong base at about room temperature in methanol, the methanolic solution is mixed with sufficient water to precipitate the cinchonidine in a form which is easy to filter. After removal of the precipitated cinchonidine, acidification yields a product enriched in d 2-(6-methoxy-2-napthyl)propionic acid.Type: GrantFiled: January 13, 1975Date of Patent: October 26, 1976Assignee: Syntex CorporationInventor: Pasquale Gallegra
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Patent number: 3980699Abstract: 2-Naphthyl acetic acid derivatives and the corresponding amides, esters, hydroxamic acids and addition salts thereof, optionally substituted at the .alpha.-position on the acetic acid moiety and/or at position 6 and/or at positions 1, 4, 7 or 8 on the naphthyl ring and optionally saturated at positions 3 and 4, are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. A pharmaceutical method of effecting treatment of inflammation, pain, pyrexia and pruritus by the administration of naphthyl acetic acid derivatives. A pharmaceutical composition for use in the treatment of the above maladies comprising a naphthyl acetic acid derivative.Type: GrantFiled: August 5, 1974Date of Patent: September 14, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 3979458Abstract: Preparation of .alpha.,.beta.-unsaturated carbocyclic ketones by reacting an enol lactone with a carbanion generated by treatment of a methylphosphonate or a mono-substituted methylphosphonate with base.Type: GrantFiled: January 10, 1975Date of Patent: September 7, 1976Assignee: Syntex CorporationInventor: John H. Fried
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Patent number: 3978124Abstract: 2-Naphthyl acetic acid derivatives and the corresponding amides, esters, hydroxamic acids and addition salts thereof, optionally substituted at the .alpha.-position on the acetic acid moiety and/or at position 6 and/or at positions 1, 4, 7 or 8 on the naphthyl ring and optionally saturated at positions 3 and 4, are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. A pharmaceutical method of effecting treatment of inflammation, pain, pyrexia and pruritus by the administration of naphthyl acetic acid derivatives. A pharmaceutical composition for use in the treatment of the above maladies comprising a naphthyl acetic acid derivative.Type: GrantFiled: March 17, 1975Date of Patent: August 31, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian J. Harrison
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Patent number: 3978116Abstract: 2-Naphthyl acetic acid derivatives and the corresponding amides, esters, hydroxamic acids and addition salts thereof, optionally substituted at the .alpha.-position on the acetic acid moiety and/or at position 6 and/or at positions 1, 4, 7 or 8 on the naphthyl ring and optionally saturated at positions 3 and 4, are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. A pharmaceutical method of effecting treatment of inflammation, pain, pyrexia and pruritus by the administration of naphthyl acetic acid derivatives. A pharmaceutical composition for use in the treatment of the above maladies comprising a naphthyl acetic acid derivative.Type: GrantFiled: March 17, 1975Date of Patent: August 31, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 3975432Abstract: 2-(6-Methoxy-2-naphthyl)propionic acid is prepared by reacting di(6-methoxy-2-naphthyl)-zinc or 6-methoxy-2-naphthylzinc halide with a lower alkyl 2-halopropionate in a suitable solvent to form a lower alkyl 2-(6-methoxy-2-naphthyl)propionate and hydrolyzing the ester group thereof. The product has anti-inflammatory, analgesic and anti-pyretic activities.Type: GrantFiled: February 21, 1974Date of Patent: August 17, 1976Assignee: Syntex CorporationInventor: Francisco Alvarez
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Patent number: 3960957Abstract: New compounds, 2-(6'-methoxynaphth-2'-yl)propylene oxide, 2-(6'-methoxynaphth-2'-yl)propionaldoxime, 2-hydroxy-2-(6'-methoxynaphth-2'-yl)-propionitrile, 2-(6'methoxynaphth-2'-yl)acrylonitrile, 2-(6'-methoxynaphth-2'-yl)acrylic acid, the corresponding 5'-halo compounds and 2-(5'-halo-6'-methoxynaphth-2'-yl)propionaldehyde are useful intermediates in producing 2-(6'-methoxynaphth-2'-yl)propionic acid and the corresponding 5'-halo acids from 6-methoxy-2-acetylnaphthalene and the corresponding 5-halo compounds. The 2-propionic acids are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. The 2-propionaldehydes, obtained from the 2-acetyl compounds by way of the 2-propylene oxide, can be converted directly to the 2-propionic acids by way of the 2-propionaldoximes and the 2-propionitriles or more directly by Jones oxidation.Type: GrantFiled: January 10, 1975Date of Patent: June 1, 1976Assignee: Syntex CorporationInventor: Francisco Sanchez Alvarez
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Patent number: 3960936Abstract: 2-(2'-Naphthyl) acetaldehyde derivatives optionally substituted at the 2 position and/or positions C-1',4',5',7' or 8'; and/or position C-6' or positions C-5' and 7' exhibit anti-inflammatory, analgesic, antipyretic and anti-pruritic activity.Type: GrantFiled: April 25, 1974Date of Patent: June 1, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 3958012Abstract: The d 2-(6-substituted-2-naphthyl)propanals of this invention are prepared by oxidizing the corresponding 2-(6-substituted-2-naphthyl)-1-propanols or by reducing d 2-(6-substituted-2-naphthyl)propionic acids, the 6-substituent being a methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, methoxy, methoxymethyloxy, difluoromethoxy, methylthio, methoxymethylthio or difluoromethylthio group. The products have anti-inflammatory, analgesic and antipyretic activities.Type: GrantFiled: March 27, 1975Date of Patent: May 18, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 3947472Abstract: 2-(2'-Naphthyl) acetaldehyde derivatives optionally substituted at the 2 position and/or positions C-1',4',5',7' or 8'; and/or position C-6' or positions C-5' and 7' exhibit anti-inflammatory, analgesic, antipyretic and anti-pruritic activity.Type: GrantFiled: July 29, 1974Date of Patent: March 30, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 3942641Abstract: This invention relates to a method of fertility control by use of novel cyclic progestogen-interrupted estrogen oral contraceptive regimens. Considering the first day of menstrual flow as day one of a 28 day medication administration cycle, a combined formulation of estrogen and progestogen substances is administered on the 3rd, 4th, 5th or 6th day of the cycle and every second or third day thereafter through, and including, the 23rd, 24th, 25th, 26th, 27th or 28th day of the cycle, and a formulation having only a progestogen substance as the active component is administered on the 4th, 5th, 6th, or 7th day of the cycle and every day thereafter on which a combination formulation is not administered, through, and including, the 22nd, 23rd, 24th, 25th, 26th, 27th or 28th day of the cycle.Type: GrantFiled: March 24, 1975Date of Patent: March 9, 1976Assignee: Syntex CorporationInventor: Eugene J. Segre
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Patent number: 3936528Abstract: This application describes analgesic formulations including d 2-(6-methoxy-2-naphthyl)propionic acid, or a pharmaceutically acceptable salt or ester thereof, in combination with at least one central nervous system active analgesic compound. Analgesic activity of the combination is greater than that obtained with either of the components alone, thus demonstrating enhanced analgesia which can be obtained therewith.Type: GrantFiled: February 13, 1974Date of Patent: February 3, 1976Assignee: Syntex CorporationInventor: Martin Katz
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Patent number: 3935273Abstract: 2-(2'-Naphthyl) acetaldehyde derivatives optionally substituted at the 2 position and/or positions C-1',4',5',7' or 8'; and/or position C-6' or positions C-5' and 7' exhibit anti-inflammatory, analgesic, antipyretic and anti-pruritic activity.Type: GrantFiled: April 25, 1974Date of Patent: January 27, 1976Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 3932635Abstract: This invention relates to a method of fertility control by use of novel cyclic progestogen-interrupted estrogen oral contraceptive regimens. Considering the first day of menstrual flow as day one of a 28 day medication administration cycle, a combined formulation of estrogen and progestogen substances is administered on the 3rd, 4th, 5th or 6th day of the cycle and every second or third day thereafter through, and including, the 23rd, 24th, 25th, 26th, 27th or 28th day of the cycle, and a formulation having only a progestogen substance as the active component is administered on the 4th, 5th, 6th, or 7th day of the cycle and every day thereafter on which a combination formulation is not administered, through, and including, the 22nd, 23rd, 24th, 25th, 26th, 27th or 28th day of the cycle.Type: GrantFiled: May 5, 1972Date of Patent: January 13, 1976Assignee: Syntex CorporationInventor: Eugene J. Segre