Five-membered Alicyclic Ring Containing Patents (Class 568/838)
  • Patent number: 4291175
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 22, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4291174
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 22, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4289910
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 15, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288630
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288633
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288629
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288632
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4278818
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: July 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4273947
    Abstract: 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: Grant
    Filed: January 31, 1979
    Date of Patent: June 16, 1981
    Assignee: Allied Chemical Corporation
    Inventor: Miroslav Novotny
  • Patent number: 4271091
    Abstract: 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: Grant
    Filed: June 17, 1978
    Date of Patent: June 2, 1981
    Assignee: Standard Oil Company
    Inventors: Robert K. Grasselli, Dev D. Suresh
  • Patent number: 4263447
    Abstract: 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: Grant
    Filed: July 16, 1979
    Date of Patent: April 21, 1981
    Assignee: Union Carbide Corporation
    Inventors: Benjamin Phillips, Walter J. Skraba, Daniel W. McNeil
  • Patent number: 4259528
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259535
    Abstract: 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: Grant
    Filed: January 28, 1980
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4259529
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4256745
    Abstract: 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: Grant
    Filed: March 2, 1978
    Date of Patent: March 17, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4243611
    Abstract: 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: Grant
    Filed: April 2, 1979
    Date of Patent: January 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4228104
    Abstract: 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: Grant
    Filed: April 2, 1979
    Date of Patent: October 14, 1980
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4225508
    Abstract: 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: Grant
    Filed: July 5, 1979
    Date of Patent: September 30, 1980
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4220795
    Abstract: 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: Grant
    Filed: August 14, 1978
    Date of Patent: September 2, 1980
    Assignee: Miles Laboratories, Inc.
    Inventors: Harold C. Kluender, Henry C. Arndt
  • Patent number: 4219451
    Abstract: 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: Grant
    Filed: August 3, 1979
    Date of Patent: August 26, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt
  • Patent number: 4215068
    Abstract: 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: Grant
    Filed: April 2, 1979
    Date of Patent: July 29, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Ching-Yong Wu, Harold E. Swift
  • Patent number: 4210767
    Abstract: 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: Grant
    Filed: March 23, 1979
    Date of Patent: July 1, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt
  • Patent number: 4206151
    Abstract: 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: Grant
    Filed: December 21, 1978
    Date of Patent: June 3, 1980
    Assignee: American Cyanamid Company
    Inventor: Charles V. Grudzinskas
  • Patent number: 4204079
    Abstract: 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: Grant
    Filed: July 12, 1978
    Date of Patent: May 20, 1980
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4204073
    Abstract: A process for producing trimethyl oxo or hydroxy substituted cycopentenone food coloring agents including intermediates in this process.
    Type: Grant
    Filed: April 6, 1979
    Date of Patent: May 20, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Frank Kienzle
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4197245
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the A.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: April 8, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4195178
    Abstract: 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: Grant
    Filed: October 2, 1978
    Date of Patent: March 25, 1980
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, Jr.
  • Patent number: 4191696
    Abstract: 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: Grant
    Filed: July 24, 1978
    Date of Patent: March 4, 1980
    Assignee: Allied Chemical Corporation
    Inventors: Benjamin S. Tovrog, Steven E. Diamond, Frank Mares
  • Patent number: 4181810
    Abstract: 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: Grant
    Filed: November 16, 1977
    Date of Patent: January 1, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel
  • Patent number: 4181798
    Abstract: 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: Grant
    Filed: October 2, 1978
    Date of Patent: January 1, 1980
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, Jr.
  • Patent number: 4176236
    Abstract: 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: Grant
    Filed: April 6, 1977
    Date of Patent: November 27, 1979
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4173585
    Abstract: 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: Grant
    Filed: August 10, 1978
    Date of Patent: November 6, 1979
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Takao Yoshida, Braja D. Mookherjee, Venkatesh Kamath, John B. Hall, William I. Taylor, Frederick L. Schmitt
  • Patent number: 4172839
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 30, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4171460
    Abstract: 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: Grant
    Filed: April 6, 1977
    Date of Patent: October 16, 1979
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4170597
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: October 9, 1979
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4165436
    Abstract: 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: Grant
    Filed: April 5, 1978
    Date of Patent: August 21, 1979
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4163758
    Abstract: 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: Grant
    Filed: September 6, 1978
    Date of Patent: August 7, 1979
    Assignee: Sagami Chemical Research Center
    Inventors: Kiyosi Kondo, Daiei Tunemoto, Teruo Umemoto
  • Patent number: 4163865
    Abstract: 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: Grant
    Filed: April 3, 1978
    Date of Patent: August 7, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
  • Patent number: 4149020
    Abstract: 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: Grant
    Filed: April 5, 1978
    Date of Patent: April 10, 1979
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Venkatesh Kamath, Braja D. Mookherjee, Frederick L. Schmitt
  • Patent number: 4140863
    Abstract: 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: Grant
    Filed: June 17, 1977
    Date of Patent: February 20, 1979
    Assignee: The Upjohn Company
    Inventor: Roy A. Johnson
  • Patent number: 4134924
    Abstract: 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: Grant
    Filed: August 11, 1977
    Date of Patent: January 16, 1979
    Assignee: Union Carbide Corporation
    Inventors: Benjamin Phillips, Walter J. Skraba
  • Patent number: 4132726
    Abstract: 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: Grant
    Filed: December 22, 1975
    Date of Patent: January 2, 1979
    Assignee: Teijin Limited
    Inventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto, Sadakazu Matsubara
  • Patent number: 4127736
    Abstract: An asymmetric synthesis of optically active prostaglandin F.sub.2.alpha. from cyclopentadiene including intermediates in this synthesis.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: November 28, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Naresh K. Chadha, John J. Partridge, Jr., Milan R. Uskokovic
  • Patent number: 4113967
    Abstract: This disclosure describes novel erythro 15,16-dioxy prostenoic acids and esters useful as bronchodilators, hypotensives and gastric acid secretion inhibitors.
    Type: Grant
    Filed: February 11, 1977
    Date of Patent: September 12, 1978
    Assignee: American Cyanamid Company
    Inventor: Martin Joseph Weiss
  • Patent number: 4113968
    Abstract: 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: Grant
    Filed: September 26, 1975
    Date of Patent: September 12, 1978
    Assignee: Kuraray Co., Ltd.
    Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi
  • Patent number: 4107181
    Abstract: 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: Grant
    Filed: February 14, 1977
    Date of Patent: August 15, 1978
    Assignee: Regent of the University of California
    Inventor: David A. Evans
  • Patent number: 4103098
    Abstract: 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: Grant
    Filed: September 12, 1977
    Date of Patent: July 25, 1978
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4089897
    Abstract: 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: Grant
    Filed: May 10, 1976
    Date of Patent: May 16, 1978
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Todd R. Williams, Larry M. Sirvio
  • Patent number: 4090019
    Abstract: 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: Grant
    Filed: January 31, 1977
    Date of Patent: May 16, 1978
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Todd R. Williams, Larry M. Sirvio