The Hetero Ring Is Five-membered Patents (Class 549/229)
  • Patent number: 4734513
    Abstract: 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: Grant
    Filed: March 31, 1986
    Date of Patent: March 29, 1988
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventor: Nicholas J. Hrib
  • Patent number: 4729842
    Abstract: 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: Grant
    Filed: February 28, 1986
    Date of Patent: March 8, 1988
    Assignee: Chevron Research Company
    Inventor: Robert H. Wollenberg
  • Patent number: 4704401
    Abstract: 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: Grant
    Filed: December 6, 1984
    Date of Patent: November 3, 1987
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: William L. Studt, Richard L. Riley, George H. Douglas
  • Patent number: 4699986
    Abstract: 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: Grant
    Filed: August 26, 1985
    Date of Patent: October 13, 1987
    Assignee: Hofmann-La Roche Inc.
    Inventors: Christian N. Hubschwerlen, Gerard Schmid
  • Patent number: 4695391
    Abstract: 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: Grant
    Filed: September 4, 1986
    Date of Patent: September 22, 1987
    Assignee: Chevron Research Company
    Inventor: Thomas F. Buckley
  • Patent number: 4677103
    Abstract: Novel labdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: June 30, 1987
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
  • Patent number: 4666904
    Abstract: Novel aminoacyllabdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: May 19, 1987
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Raymond W. Kosley, Jr., Robert J. Cherill
  • Patent number: 4663469
    Abstract: 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: Grant
    Filed: December 10, 1984
    Date of Patent: May 5, 1987
    Assignee: Hoffman-La Roche Inc.
    Inventors: Chung-Chen Wei, Manfred Weigele
  • Patent number: 4663467
    Abstract: 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: Grant
    Filed: March 5, 1984
    Date of Patent: May 5, 1987
    Assignee: The Dow Chemical Company
    Inventors: William J. Kruper, Jr., David V. Dellar
  • Patent number: 4658041
    Abstract: 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: Grant
    Filed: September 24, 1982
    Date of Patent: April 14, 1987
    Assignee: The Dow Chemical Company
    Inventor: James M. Renga
  • Patent number: 4654331
    Abstract: 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: Grant
    Filed: August 23, 1984
    Date of Patent: March 31, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Burton G. Christensen
  • Patent number: 4585566
    Abstract: 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: Grant
    Filed: November 21, 1984
    Date of Patent: April 29, 1986
    Assignee: Chevron Research Company
    Inventor: Robert H. Wollenberg
  • Patent number: 4554358
    Abstract: 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: Grant
    Filed: November 16, 1984
    Date of Patent: November 19, 1985
    Assignee: Kanebo, Ltd.
    Inventors: Yasushi Takebe, Koji Iuchi, Goro Tsukamoto
  • Patent number: 4515972
    Abstract: 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: Grant
    Filed: October 19, 1983
    Date of Patent: May 7, 1985
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jagabandhu Das, Martin F. Haslanger
  • Patent number: 4487779
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: December 11, 1984
    Assignee: William H. Rorer, Inc.
    Inventors: William L. Studt, Richard L. Riley, George H. Douglas
  • Patent number: 4483994
    Abstract: 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: Grant
    Filed: February 22, 1983
    Date of Patent: November 20, 1984
    Assignee: The Halcon SD Group, Inc.
    Inventor: Stephen E. Jacobson
  • Patent number: 4479947
    Abstract: 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: Grant
    Filed: June 7, 1982
    Date of Patent: October 30, 1984
    Assignee: Merck & Co., Inc.
    Inventor: Burton G. Christensen
  • Patent number: 4453005
    Abstract: Substituted phenylalkenoic acids and esters of the formula: ##STR1## having useful pharmaceutical activity and processes for their preparation are disclosed.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: June 5, 1984
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Patrice C. Belanger, Claude Dufresne, John W. Gillard, Haydn W. R. Williams
  • Patent number: 4434173
    Abstract: 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: Grant
    Filed: November 15, 1982
    Date of Patent: February 28, 1984
    Assignee: Pfizer Inc.
    Inventor: Willard M. Welch, Jr.
  • Patent number: 4428806
    Abstract: 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: Grant
    Filed: September 28, 1982
    Date of Patent: January 31, 1984
    Assignee: Kanebo Ltd.
    Inventors: Fumio Sakamoto, Shoji Ikeda, Goro Tsukamoto, Isamu Utsumi
  • Patent number: 4423235
    Abstract: 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: Grant
    Filed: April 14, 1980
    Date of Patent: December 27, 1983
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Michel Burgard, Marc D. Piteau, Alain J. Rollat, Jean-Pierre G. Senet
  • Patent number: 4390708
    Abstract: 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: Grant
    Filed: February 23, 1981
    Date of Patent: June 28, 1983
    Assignee: Terochem Laboratories Ltd.
    Inventors: Robert J. Stokowski, Gerard Tertzakian, Tomoki C. S. Ruo
  • Patent number: 4353831
    Abstract: 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: Grant
    Filed: February 2, 1981
    Date of Patent: October 12, 1982
    Assignee: The Dow Chemical Company
    Inventors: Paul E. Strege, James M. Renga
  • Patent number: 4344881
    Abstract: 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: Grant
    Filed: February 2, 1981
    Date of Patent: August 17, 1982
    Assignee: The Dow Chemical Company
    Inventors: Paul E. Strege, James M. Renga
  • Patent number: 4342693
    Abstract: 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: Grant
    Filed: April 27, 1981
    Date of Patent: August 3, 1982
    Assignee: Kanebo Ltd.
    Inventors: Fumio Sakamoto, Shoji Ikeda, Goro Tsukamoto, Isamu Utsumi
  • Patent number: 4338450
    Abstract: Carbamate-sulfenyl-carba moyl fluoride compounds are valuable insecticidal compositions and are also useful intermediates in the production of bis-carbamate compounds.
    Type: Grant
    Filed: December 1, 1975
    Date of Patent: July 6, 1982
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4332729
    Abstract: 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: Grant
    Filed: July 17, 1981
    Date of Patent: June 1, 1982
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Roy A. Periana-Pillai
  • Patent number: 4331604
    Abstract: 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: Grant
    Filed: July 17, 1981
    Date of Patent: May 25, 1982
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Roy A. Periana-Pillai