The Hetero Ring Is Five-membered Patents (Class 549/229)
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Patent number: 4734513Abstract: A method of regioselectively and stereoselectively synthesizing forskolin (8,13-epoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetrahydroxylabd-14-en-11-on e) from 9-deoxyforskolin (8,13-epoxy-1.alpha.,6.beta.,7.beta.-trihydroxylabd-14-en-11-one) with a good yield is described. In a preferred embodiment, it comprises an enol ether formation from 8,13-epoxy-1.alpha.,6.beta.,7.beta.-trihydroxylabd-14-en-11-one-6,7-carbon ate, oxidation of the enol ether with a suitable peroxy acid to obtain 11,12-dehydro-8,13-epoxy-11-methoxy-1.alpha.,6.beta.,7.beta.,9.beta.-tetra hydrolabd-14-ene-6,7-carbonate and hydrolysis of the latter under an acidic condition to obtain 8,13-epoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetrahydroxylabd-14-en-11-one -6,7-carbonate. As an alternative way of protecting the two hydroxy groups at carbon-6 and carbon-7, they may also be converted to dimethyl acetal during the synthetic sequence. Four compounds produced in the synthetic scheme as intermediates, namely, 9,11-dehydro-8,13-epoxy-11-methoxy-1.Type: GrantFiled: March 31, 1986Date of Patent: March 29, 1988Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventor: Nicholas J. Hrib
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Patent number: 4729842Abstract: Disclosed are additives which are useful as dispersants in marine crankcase oils and hydraulic oils, lubricating oils. In particular, disclosed are nitrogen-containing lubricating oil dispersants having at least one primary or secondary amino group which have been modified by treatment with a cyclic carbonate.Type: GrantFiled: February 28, 1986Date of Patent: March 8, 1988Assignee: Chevron Research CompanyInventor: Robert H. Wollenberg
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Patent number: 4704401Abstract: This invention relates to a method of lowering blood pressure in humans and mammals using 2,6-disubstituted phenyl amidinoureas in which the phenyl ring is additionally substituted by a hydroxy, alkoxy, aralkoxy, alkenyloxy, alkynyloxy, haloacyloxy, or acyloxy group and to novel 2,6-disubstituted phenyl amidinoureas which possess pharmaceutical properties, including blood pressure lowering activity.Type: GrantFiled: December 6, 1984Date of Patent: November 3, 1987Assignee: Rorer Pharmaceutical CorporationInventors: William L. Studt, Richard L. Riley, George H. Douglas
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Patent number: 4699986Abstract: There is presented optically uniform .beta.-lactams of the formulae ##STR1## wherein Z is a readily cleavable acyl group, R.sup.1 is amino or a group convertible into amino, R.sup.2 is hydrogen or a readily cleavable protecting group and R.sup.3 and R.sup.4 each are a lower hydrocarbon group which optionally contains oxygen and which is attached via a carbon atom, whereby these groups can also be joined with one another to form a ring, with the proviso that R.sup.1 is a readily cleavable acylamino when R.sup.2 is hydrogen,and the corresponding optical antipodes, their manufacture and use in the manufacture of antimicrobially-active .beta.-lactams as well as novel intermediates usable in their manufacture.Type: GrantFiled: August 26, 1985Date of Patent: October 13, 1987Assignee: Hofmann-La Roche Inc.Inventors: Christian N. Hubschwerlen, Gerard Schmid
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Patent number: 4695391Abstract: Disclosed are additives which are useful as dispersants in marine crankcase oils, hydraulic oils, and lubricating oils. In particular, disclosed are polyamino alkenyl or alkyl succinimides modified by reaction with a compound of the formula: ##STR1## wherein R.sub.4 is selected from the group consisting of a divalent hydrocarbyl group of from 2 to 30 carbon atoms with the proviso that the hydrocarbyl carbon atom bound to one ##STR2## group is not also bound to the other ##STR3## group and --R.sub.5 --OR.sub.5 --.sub.p wherein R.sub.5 is alkylene of from 2 to 5 carbon atoms and p is an integer of from 1 to 100; X is selected from the group consisting of bromo, chloro and --OR.sub.6 wherein R.sub.6 is selected from the group consisting of alkyl of from 1 to 6 carbon atoms, phenyl and phenyl substituted with 1 to 2 substituents selected from the group consisting of chloro, bromo, nitro, alkyl of from 1 to 6 carbon atoms and trifluoromethyl; and m is independently an integer of from 0 to 1.Type: GrantFiled: September 4, 1986Date of Patent: September 22, 1987Assignee: Chevron Research CompanyInventor: Thomas F. Buckley
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Patent number: 4677103Abstract: Novel labdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: October 20, 1986Date of Patent: June 30, 1987Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4666904Abstract: Novel aminoacyllabdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: October 20, 1986Date of Patent: May 19, 1987Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
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Patent number: 4663469Abstract: A novel enantiomeric systhesis from ascorbic acid of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-azetidinone-1-sulfate, an intermediate for an antibiotic compound.Type: GrantFiled: December 10, 1984Date of Patent: May 5, 1987Assignee: Hoffman-La Roche Inc.Inventors: Chung-Chen Wei, Manfred Weigele
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Patent number: 4663467Abstract: This invention is a composition comprising(a) a p-hydrocarbylphenylporphyrinato chromium or aluminum with axial counterions; and(b) an aliphatic amine, a heterocyclic amine, an aromatic amine, a phosphine or a phosphine oxide.Another aspect of this invention is a process for the preparation of an alkylene carbonate which comprises contacting an epoxide with a carbon dioxide in the presence of a catalytic amount of the hereinbefore-described composition.Type: GrantFiled: March 5, 1984Date of Patent: May 5, 1987Assignee: The Dow Chemical CompanyInventors: William J. Kruper, Jr., David V. Dellar
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Patent number: 4658041Abstract: Carbonate compounds are prepared by equilibrium interchange of carbonate functionality between lower alkyl carbonates especially dimethyl carbonate and alkyl halides such as allyl chloride at about 50.degree. C. to about 250.degree. C. in the presence of an initiator such as homogeneous or heterogeneous amines, phosphines, and ammonium or phosphonium quaternary salts.Type: GrantFiled: September 24, 1982Date of Patent: April 14, 1987Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4654331Abstract: The (5-R-2-oxo-1,3-dioxolen-4-yl)methyl moiety: ##STR1## wherein R is loweralkyl of 1-6 carbon atoms, especially methyl or t-butyl; when utilized as an ester on a pharmaceutical having a carboxylic acid functionality, enhances oral absorption of the pharmaceutical. This effect is applicable to a broad range of pharmaceutically active substances, including antibiotics, and antihypertensives as well as other classes of therapeutic agents.Type: GrantFiled: August 23, 1984Date of Patent: March 31, 1987Assignee: Merck & Co., Inc.Inventor: Burton G. Christensen
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Patent number: 4585566Abstract: Disclosed are additives which are useful as dispersants in marine crankcase oils and hydraulic oils, lubricating oils. In particular, disclosed are nitrogen-containing lubricating oil dispersants having at least one primary or secondary amino group which have been modified by treatment with a cyclic carbonate.Type: GrantFiled: November 21, 1984Date of Patent: April 29, 1986Assignee: Chevron Research CompanyInventor: Robert H. Wollenberg
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Patent number: 4554358Abstract: 4-Chloro-4-methyl-5-methylene-1,3-dioxolane-2-one is useful as an intermediate for the synthesis of 4-chloromethyl-5-methyl-1,3-dioxolene-2-one which, in turn, finds use as a modifying agent for making various prodrugs.Said intermediate compound gives said objective compound in a good yield by a rearrangement reaction.Type: GrantFiled: November 16, 1984Date of Patent: November 19, 1985Assignee: Kanebo, Ltd.Inventors: Yasushi Takebe, Koji Iuchi, Goro Tsukamoto
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Patent number: 4515972Abstract: A method is provided for preparing intermediates for use in preparing 7-oxabicycloheptane prostaglandin derivatives which method includes the steps of reducing (exo)hexa hydro-4,5-epoxyisobenzofuran-1,3-dione to the corresponding diol, subjecting the diol to a chloroformylation reaction to form a compound of the structure ##STR1## reacting the above with pyridine to form the cyclic carbonate reacting the cyclic carbonate with an alkanol to form the alcohol of the strucure ##STR2## tosylating the above alcohol to form the tosylate and subjecting the above tosylate to a cyanation reaction to form the cyano carbonate of the structure ##STR3## The cyano carbonate may then be reduced by, for example, reaction with diisobutyl aluminum hydride to form the hemiacetal ##STR4## which is used in preparing 7-oxabicycloheptane prostaglandin derivatives as disclosed in U.S. Pat. No. 4,143,054.New intermediates of the structures set out above, other than the hemiacetal, are also provided.Type: GrantFiled: October 19, 1983Date of Patent: May 7, 1985Assignee: E. R. Squibb & Sons, Inc.Inventors: Jagabandhu Das, Martin F. Haslanger
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Patent number: 4487779Abstract: This invention relates to a method of lowering blood pressure in humans and mammals using 2,6-disubstituted phenyl amidinoureas in which the phenyl ring is additionally substituted by a hydroxy, alkoxy, aralkoxy, alkenyloxy, alkynyloxy, haloacyloxy, or acyloxy group and to novel 2,6-disubstituted phenyl amidinoureas which possess pharmaceutical properties, including blood pressure lowering activity.Type: GrantFiled: July 6, 1981Date of Patent: December 11, 1984Assignee: William H. Rorer, Inc.Inventors: William L. Studt, Richard L. Riley, George H. Douglas
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Patent number: 4483994Abstract: A process for the production of alkylene carbonates, such as propylene carbonate, is disclosed. The process involves reacting the desired olefin with a thallic oxide or a weak acid thallic salt with carbon dioxide in an aqueous, organic solvent containing, halogen-free system.Type: GrantFiled: February 22, 1983Date of Patent: November 20, 1984Assignee: The Halcon SD Group, Inc.Inventor: Stephen E. Jacobson
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Patent number: 4479947Abstract: The (5-R-2-oxo-1,3-dioxolen-4-yl)methyl moiety: ##STR1## wherein R is loweralkyl of 1-6 carbon atoms, especially methyl or t-butyl; when utilized as an ester on a pharmaceutical having a carboxylic acid functionality, enhances oral absorption of the pharmaceutical. This effect is applicable to a broad range of pharmaceutically active substances, including antibiotics, and antihypertensives as well as other classes of therapeutic agents.Type: GrantFiled: June 7, 1982Date of Patent: October 30, 1984Assignee: Merck & Co., Inc.Inventor: Burton G. Christensen
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Patent number: 4453005Abstract: Substituted phenylalkenoic acids and esters of the formula: ##STR1## having useful pharmaceutical activity and processes for their preparation are disclosed.Type: GrantFiled: December 6, 1982Date of Patent: June 5, 1984Assignee: Merck Frosst Canada, Inc.Inventors: Patrice C. Belanger, Claude Dufresne, John W. Gillard, Haydn W. R. Williams
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Patent number: 4434173Abstract: Derivatives of 4,5-di(hydroxymethyl)-2-oxo-1,3-dioxole in which one hydroxy group has been esterified through the carboxy group of ampicillin or amoxicillin, and the other hydroxy group has been esterified through the carboxy group of sulbactam (penicillanic acid 1,1-dioxide), are useful as antibacterial agents. Certain novel compounds, which are useful as intermediates to the aforesaid antibacterial agents, are also disclosed.Type: GrantFiled: November 15, 1982Date of Patent: February 28, 1984Assignee: Pfizer Inc.Inventor: Willard M. Welch, Jr.
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Patent number: 4428806Abstract: A process for producing a brominated 1,3-dioxolen-2-one of the following general formula (I) ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group, or an aryl group, and R.sub.2 represents a hydrogen atom, or R.sub.1 and R.sub.2 may be bonded together to form --(CH.sub.2).sub.n -- in which n represents an integer of 3 to 5, which comprises reacting a compound of the following formula (II) ##STR2## wherein R.sub.1 and R.sub.2 are as defined, with bromine under radical generating conditions.Type: GrantFiled: September 28, 1982Date of Patent: January 31, 1984Assignee: Kanebo Ltd.Inventors: Fumio Sakamoto, Shoji Ikeda, Goro Tsukamoto, Isamu Utsumi
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Patent number: 4423235Abstract: The invention relates to new industrial products of the general formula ##STR1## a process for the manufacture of these products and their application in hydrometallurgy.According to the invention, R is in particular an alkyl, cycloalkyl, aryl, aralkyl, carboxylate, polyoxyethylene, polyester or polycarbonate group. The process consists in reacting an alcohol or a polyol, ROH, with 2,3-dioxycarbonylpropyl chloroformate, at between -10.degree. and +20.degree. C., in the presence of an acid acceptor.Application: the compounds according to the invention are extraction agents for hydrometallurgy, which can be used in dilute solution.Type: GrantFiled: April 14, 1980Date of Patent: December 27, 1983Assignee: Societe Nationale des Poudres et ExplosifsInventors: Michel Burgard, Marc D. Piteau, Alain J. Rollat, Jean-Pierre G. Senet
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Patent number: 4390708Abstract: A process is provided for producing oxalyl chloride by first photochemically chlorinating ethylene carbonate to form tetrachloroethylene carbonate and hydrogen chloride and then decomposing the tetrachloroethylene carbonate to oxalyl chloride and phosgene. The chlorination reaction is performed in a reaction vessel having an illuminated side arm conduit of narrow cross-sectional area. Chlorine is introduced at the base of the conduit and together with the hydrogen chloride evolved in the reaction continuously circulates the ethylene carbonate-chlorine reaction mixture through the narrow reaction zone within the conduit. The temperature of the ethylene carbonate-chlorine reaction mixture is controlled in the range of 70.degree. to 100.degree. C., preferably in the range of 79.degree. to 81.degree. C. The tetrachloroethylene carbonate is decomposed by heating same with a catalytic amount of a tertiary amine or amide.Type: GrantFiled: February 23, 1981Date of Patent: June 28, 1983Assignee: Terochem Laboratories Ltd.Inventors: Robert J. Stokowski, Gerard Tertzakian, Tomoki C. S. Ruo
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Patent number: 4353831Abstract: Hexachloroacetone and a vicinal alkylene diol react when heated together in the presence of a weak base to produce chloroform and the cyclic alkylene carbonate. The chloroform distills from the reaction mixture substantially as it is formed and the alkylene carbonate is readily separable from the residual mixture.Type: GrantFiled: February 2, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventors: Paul E. Strege, James M. Renga
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Patent number: 4344881Abstract: A lower alkyl trichloroacetate and a vicinal alkylene diol react when heated together in the presence of a weak base to produce chloroform, a lower alkanol, and the cyclic alkylene carbonate. The chloroform and lower alkanol distill from the reaction mixture substantially as formed and the alkylene carbonate is readily separable from the residual mixture.Type: GrantFiled: February 2, 1981Date of Patent: August 17, 1982Assignee: The Dow Chemical CompanyInventors: Paul E. Strege, James M. Renga
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Patent number: 4342693Abstract: A 1,3-dioxolen-2-one derivative of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group, or an aryl group, R.sub.2 represents a hydrogen atom, or may be taken together with R.sub.1 to form a divalent carbon chain residue, and x represents a halogen atom.The above compounds can be prepared by reacting a compound of the general formula ##STR2## with a halogenating agent, and are useful as protective group-introducing reagents for introducing protective groups into reagents in various chemical reactions, or as modifiers for prodrug preparation in medicine.Type: GrantFiled: April 27, 1981Date of Patent: August 3, 1982Assignee: Kanebo Ltd.Inventors: Fumio Sakamoto, Shoji Ikeda, Goro Tsukamoto, Isamu Utsumi
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Patent number: 4338450Abstract: Carbamate-sulfenyl-carba moyl fluoride compounds are valuable insecticidal compositions and are also useful intermediates in the production of bis-carbamate compounds.Type: GrantFiled: December 1, 1975Date of Patent: July 6, 1982Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4332729Abstract: The thermal decomposition of a halogenated aliphatic carbonate at about 100.degree. C.-300.degree. C. to produce a cyclic carbonate and an aliphatic halide is accelerated by the presence of chemically combined mercury.Type: GrantFiled: July 17, 1981Date of Patent: June 1, 1982Assignee: The Dow Chemical CompanyInventors: James M. Renga, Roy A. Periana-Pillai
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Patent number: 4331604Abstract: The thermal decomposition of a .beta.-halogenated aliphatic carbonate at about 100.degree. C.-300.degree. C. to produce a cyclic alkylene carbonate and an aliphatic halide is accelerated by the presence of a polar solvent, preferably the cyclic carbonate product. Further improvement may be obtained when there is additionally present a mercury compound.Type: GrantFiled: July 17, 1981Date of Patent: May 25, 1982Assignee: The Dow Chemical CompanyInventors: James M. Renga, Roy A. Periana-Pillai