Five-membered Alicyclic Ring Containing Patents (Class 568/838)
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Patent number: 4291175Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 22, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4291174Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 22, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4289910Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 15, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288630Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288633Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288629Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288632Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4278818Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-13,14-dihydro-PG.sub.2 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: July 14, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4273947Abstract: A process is described for the heterogeneous hydrogenation of fluorine-containing alkyl, cycloalkyl, and benzene carboxylic acids to the corresponding primary alcohols. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50.degree.-150.degree. C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic acid in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF.sub.3 CHClOCHF.sub.2.Type: GrantFiled: January 31, 1979Date of Patent: June 16, 1981Assignee: Allied Chemical CorporationInventor: Miroslav Novotny
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Patent number: 4271091Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.Type: GrantFiled: June 17, 1978Date of Patent: June 2, 1981Assignee: Standard Oil CompanyInventors: Robert K. Grasselli, Dev D. Suresh
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Patent number: 4263447Abstract: Allylic cycloalkenols and/or allylic cycloalkenol esters are prepared by autoxidation of the corresponding cycloolefins using elemental oxygen contacted with solutions of cycloolefins containing catalytic amounts of soluble cobalt and copper compounds with a carboxylic acid activator.Type: GrantFiled: July 16, 1979Date of Patent: April 21, 1981Assignee: Union Carbide CorporationInventors: Benjamin Phillips, Walter J. Skraba, Daniel W. McNeil
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Patent number: 4259528Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: March 31, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4259535Abstract: The present invention particularly relates to novel 2-decarboxy-2-hydroxymethyl-9-deoxy-9-methylene-5,6-didehydro-PGF.sub.1 compounds and methods for their preparation in pharmacological use.Type: GrantFiled: January 28, 1980Date of Patent: March 31, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4259529Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-13,14-dihydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: March 31, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4256745Abstract: Prostan-1-ol esters and intermediates for their preparation are described; the former compounds exhibit improved organ specificity and a longer duration of activity at lower dosages than the corresponding non-esterified prostaglandins and are useful, inter alia, in triggering abortion, inducing labor and regulating the menstrual cycle.Type: GrantFiled: March 2, 1978Date of Patent: March 17, 1981Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4243611Abstract: Prostaglandin derivatives having a 19,20-didehydro, a 19-hydroxy, or a 19-keto feature are disclosed, including processes for preparing them and the appropriate intermediates.A typical 19-hydroxy compound of this invention is 19-hydroxy-19-methyl-PGF.sub.2.alpha.Type: GrantFiled: April 2, 1979Date of Patent: January 6, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4228104Abstract: Prostaglandin derivatives having a 19,20-didehydro, a 19-hydroxy, or a 19-keto feature are disclosed, including processes for preparing them and the appropriate intermediates.A typical 19-hydroxy compound of this invention is 19-hydroxy-19-methyl-PGF.sub.2.alpha.Type: GrantFiled: April 2, 1979Date of Patent: October 14, 1980Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4225508Abstract: Prostacyclin and prostacyclin-type derivatives having a 19-hydroxy feature are disclosed, including processes for preparing them and the appropriate intermediates. The compounds are useful for pharmacological purposes such as inhibition of blood platelate aggregation.Type: GrantFiled: July 5, 1979Date of Patent: September 30, 1980Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4220795Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.Type: GrantFiled: August 14, 1978Date of Patent: September 2, 1980Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Henry C. Arndt
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Patent number: 4219451Abstract: Described are perfume compositions and processes for producing same which compositions comprise in an aroma augmenting or enhancing quantity at least one compound having the structure: ##STR1## wherein m is 0 or 1; wherein one of the lines + + + + is a carbon-carbon single bond and the other of the lines + + + + is a carbon-carbon double bond and wherein X is carbinol having the structure: ##STR2## and at least one adjuvant selected from the group consisting of natural perfume oils, synthetic perfume oils, alcohols, aldehydes, ketones other than those defined herein, esters, nitriles and lactones. Also described are colognes containing compounds having the above structure and ethanol and water.Type: GrantFiled: August 3, 1979Date of Patent: August 26, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt
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Patent number: 4215068Abstract: 1,3-Dicyanocyclopentane is prepared by the hydrocyanation of 2-cyanocyclopentene in the presence of a catalyst system comprising a zero valent nickel complex, free of carbon monoxide, and a promoting amount of a metal compound such as zinc chloride.Type: GrantFiled: April 2, 1979Date of Patent: July 29, 1980Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Harold E. Swift
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Patent number: 4210767Abstract: Described are perfume and fragrance compositions and perfumed articles including soaps, detergents, powders as well as colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones having the generic structure: ##STR1## wherein one of the lines + + + + + is a carbon-carbon double bond and the other of the lines + + + + + is a carbon-carbon single bond; wherein X is carbinol having the structure: ##STR2## or carbonyl having the structure ##STR3## wherein A' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; wherein B' is hydrogen,CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; where n is 0, 1 or 2; wherein each of the dashed lines are the same and each represents a carbon-carbon single bond or no bond; wherein A' and B' are both --CH.sub.2 -- when n is 1 or 2 and the dashed line is a carbon-carbon single bond or A' is hydrogen and B' is C.sub.2 H.sub.5 or CH.sub.3 or both A' and B' are each CH.sub.3 or A' is C.sub.2 H.sub.Type: GrantFiled: March 23, 1979Date of Patent: July 1, 1980Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt
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Patent number: 4206151Abstract: This disclosure describes novel 15-deoxy-16 hydroxy-16-substituted prostanoic acid analogs in which the C-1 carboxyl is replaced by a primary alcohol and carboxylic acid esters, carbonates and carbomates thereof. The prostanoic carbinols and carboxylic acid esters thereof described herein have utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: December 21, 1978Date of Patent: June 3, 1980Assignee: American Cyanamid CompanyInventor: Charles V. Grudzinskas
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Patent number: 4204079Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.Type: GrantFiled: July 12, 1978Date of Patent: May 20, 1980Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4204073Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.Type: GrantFiled: April 6, 1979Date of Patent: May 20, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Frank Kienzle
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4197245Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4195178Abstract: Methylenecyclopentane derivatives, for example ##STR1## wherein R.sub.2 is a blocking group such as tetrahydropyranyl, and a process for preparing them; said derivatives having utility as prostaglandin intermediates.Type: GrantFiled: October 2, 1978Date of Patent: March 25, 1980Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4191696Abstract: A new liquid phase oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a catalytic process, molecular oxygen maintains a concentration of nitro ligand in the reaction mixture. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate, In particular the metal is a Group VIII metal, especially cobalt and the nitro complex is pyridine cobalt nitro saloph. To accelerate oxidation of the substrate at given temperature, a cocatalyst is included in the reaction mixture, e.g.Type: GrantFiled: July 24, 1978Date of Patent: March 4, 1980Assignee: Allied Chemical CorporationInventors: Benjamin S. Tovrog, Steven E. Diamond, Frank Mares
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Patent number: 4181810Abstract: A process for the preparation of a propane-1,3-diol, disubstituted in the 2-position, which comprises contacting an ethanal disubstituted in the 2-position, which ethanal has the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and denote optionally substituted alkyl, cycloalkyl, aralkyl or aryl radicals or an optionally substituted heterocyclic radical, or together denote an optionally substituted divalent hydrocarbon radical with formaldehyde in the presence of an acid ion exchanger and thereafter contacting the resultant reaction product with hydrogen under hydrogenation conditions.Type: GrantFiled: November 16, 1977Date of Patent: January 1, 1980Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel
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Patent number: 4181798Abstract: Methylenecyclopentane derivatives, for example ##STR1## wherein R.sub.2 is a blocking group such as tetrahydropyranyl, and a process for preparing them; said derivatives having utility as prostaglandin intermediates.Type: GrantFiled: October 2, 1978Date of Patent: January 1, 1980Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4176236Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.Type: GrantFiled: April 6, 1977Date of Patent: November 27, 1979Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4173585Abstract: Described are perfume and fragrance compositions and perfumed articles including soaps, detergents, powders as well as colognes containing 2,2,3-trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones having the generic structure: ##STR1## wherein one of the lines +++++ is a carbon-carbon double bond and the other of the lines +++++ is a carbon-carbon single bond; wherein X is carbinol having the structure: ##STR2## or carbonyl having the structure ##STR3## wherein A' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; wherein B' is hydrogen, CH.sub.3, C.sub.2 H.sub.5 or --CH.sub.2 --; where n is 0, 1 or 2; wherein each of the dashed lines are the same and each represents a carbon-carbon single bond or no bond; wherein A' and B' are both --CH.sub.2 -- when n is 1 or 2 and the dashed line is a carbon-carbon single bond or A' is hydrogen and B' is C.sub.2 H.sub.5 or CH.sub.3 or both A' and B' are each CH.sub.3 or A' is C.sub.2 H.sub.5 and B' is CH.Type: GrantFiled: August 10, 1978Date of Patent: November 6, 1979Assignee: International Flavors & Fragrances Inc.Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt
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Patent number: 4172839Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 30, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4171460Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.Type: GrantFiled: April 6, 1977Date of Patent: October 16, 1979Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4170597Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 9, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4165436Abstract: The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharmacological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.Type: GrantFiled: April 5, 1978Date of Patent: August 21, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4163758Abstract: 2-Nitroethylcyclopentane compounds represented by the formula (I) ##STR1## wherein X represents a ##STR2## R and R.sup.1 each represents a hydrogen atom or a protective group for a hydroxy group, R.sup.2 represents an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms and R.sup.5 represents a hydrogen atom or an alkyl group havng 1 to 4 carbon atoms, which are useful as intermediates for the synthesis of prostaglandin compounds, and a process for preparing the 2-nitroethylcyclopentane compounds of the formula (I).Type: GrantFiled: September 6, 1978Date of Patent: August 7, 1979Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Daiei Tunemoto, Teruo Umemoto
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Patent number: 4163865Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.Type: GrantFiled: April 3, 1978Date of Patent: August 7, 1979Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
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Patent number: 4149020Abstract: 2,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol possesses a strong woody, oily, sandalwood note reminiscent of sandalwood oil and is especially valuable in fragrance compositions, perfumed articles and colognes.Type: GrantFiled: April 5, 1978Date of Patent: April 10, 1979Assignee: International Flavors & Fragrances Inc.Inventors: Venkatesh Kamath, Braja D. Mookherjee, Frederick L. Schmitt
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Patent number: 4140863Abstract: The present invention relates to certain 9,11-dideoxy-PGF-type compounds wherein the C-9 and C-11 carbon atoms are substituted by halogen. In particular, 9,11-chloro-, 9,11-bromo-, and 9,11-iodo-9,11-dideoxy-PGF compounds are disclosed.These compounds are particularly useful for numerous pharmacological purposes, based on their ability to stimulate mammalian smooth muscle tissue.Type: GrantFiled: June 17, 1977Date of Patent: February 20, 1979Assignee: The Upjohn CompanyInventor: Roy A. Johnson
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Patent number: 4134924Abstract: Bis-(2-cyclopentenyl) ethers are prepared by contacting a 2-cyclopentenyl carboxylate or 2-cyclopentenol with an aqueous acid solution having a pH in the range of about 1.0 to about 3.0.Type: GrantFiled: August 11, 1977Date of Patent: January 16, 1979Assignee: Union Carbide CorporationInventors: Benjamin Phillips, Walter J. Skraba
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Patent number: 4132726Abstract: Novel optically active compounds of 4-protected hydroxy-cyclopent-2-en-1-ones of the formula ##STR1## wherein R is a splittable protective group for an alcoholic hydroxyl group, and a process for preparing the 4-protected hydroxycyclopent-2-en-1-ones by oxidizing monohydroxy-protected derivatives of cyclopent-1-ene-3,5-diol expressed by the following formula ##STR2## wherein R is the same as defined above. Optically active 4-hydroxycyclopent-2-en-1-one which is an optically active isomer of the compound of formula (2); or optically active cyclopent-1-en-3,5-diol (R-isomer) and a novel diacyl derivative of the diol, a novel monoacylmonosilyl-derivative of the diol and a novel monoacylmonotetrahydropyranol-derivative of the diol, which are intermediates for the protective derivative of formula (1). Processes are also provided for preparing the protective derivatives of formula (1) by converting these intermediates by esterification, hydrolysis, enzymatic processes, etc.Type: GrantFiled: December 22, 1975Date of Patent: January 2, 1979Assignee: Teijin LimitedInventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto, Sadakazu Matsubara
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Patent number: 4127736Abstract: An asymmetric synthesis of optically active prostaglandin F.sub.2.alpha. from cyclopentadiene including intermediates in this synthesis.Type: GrantFiled: September 19, 1977Date of Patent: November 28, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Naresh K. Chadha, John J. Partridge, Jr., Milan R. Uskokovic
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Patent number: 4113967Abstract: This disclosure describes novel erythro 15,16-dioxy prostenoic acids and esters useful as bronchodilators, hypotensives and gastric acid secretion inhibitors.Type: GrantFiled: February 11, 1977Date of Patent: September 12, 1978Assignee: American Cyanamid CompanyInventor: Martin Joseph Weiss
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Patent number: 4113968Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.Type: GrantFiled: September 26, 1975Date of Patent: September 12, 1978Assignee: Kuraray Co., Ltd.Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi
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Patent number: 4107181Abstract: The novel synthesis of chemical compounds of the structures 1 and 2 is disclosed. ##STR1## Compounds 1 and 2 are shown to be useful intermediates in prostaglandin synthesis.Type: GrantFiled: February 14, 1977Date of Patent: August 15, 1978Assignee: Regent of the University of CaliforniaInventor: David A. Evans
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Patent number: 4103098Abstract: This invention comprises certain analogs PGE or 11-deoxy-PGE compounds in which the carbonyl at C-9 is replaced by methylene. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.Type: GrantFiled: September 12, 1977Date of Patent: July 25, 1978Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4089897Abstract: Geminal prostaglandins (P.G.'s) are synthesized which are represented by the general formula: ##STR1## where A is a 4 or 5 carbon atom ring-completing group (CH.sub.2).sub.1+m --X--(CH.sub.2).sub.z where m = 0, 1 or 2,Z = 0 or 1, 0<(m + z)<3, and X is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CHOH--, ##STR2## and, when m = 0 and z = 1, is also --CH=CH-- or ##STR3## Y is divalent straight chain alkylene of 4 to 8 carbon atoms or--CH.sub.2 CH=CH(CH.sub.2).sub.3 --;r is alkyl of 4 to 7 carbon atoms;Q is --CO.sub.2 H or --CH.sub.2 OH provided that it is not --CH.sub.2 OH when X = ##STR4## or Y--Q taken together may be heptyl or allyl.Type: GrantFiled: May 10, 1976Date of Patent: May 16, 1978Assignee: Minnesota Mining and Manufacturing CompanyInventors: Todd R. Williams, Larry M. Sirvio
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Patent number: 4090019Abstract: Geminal prostaglandins (P.G.'s) are synthesized which are represented by the general formula: ##STR1## where A is a 4 or 5 carbon atom ring-completing group (CH.sub.2).sub.1+m --X--(CH.sub.2).sub.z where m = 0, 1 or 2,Z = 0 or 1, 0<(m+z)<3, and X is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CHOH--, ##STR2## and, when m = 0 and z = 1, is also --CH=CH-- or ##STR3## Y is divalent straight chain alkylene of 4 to 8 carbon atoms or --CH.sub.2 CH=CH(CH.sub.2).sub.3 --;R is alkyl of 4 to 7 carbon atoms;Q is --CO.sub.2 H or --CH.sub.2 OH provided that it is not --CH.sub.2 OH when ##STR4## or Y-Q taken together may be heptyl or allyl.Type: GrantFiled: January 31, 1977Date of Patent: May 16, 1978Assignee: Minnesota Mining and Manufacturing CompanyInventors: Todd R. Williams, Larry M. Sirvio