Abstract: Novel compounds of the formula ##STR1## wherein D is hydrogen, halogen, (halo)alkyl or (halo)alkoxy; R is hydrogen, alkyl or alkoxy and R.sup.1 is the hydrocarbyl residue of a saturated oxygen-heterocyclic alcohol, are useful as herbicides.
Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo[2,2,1]hept-2Z-ene, bicyclo[2,2,1]heptane, 7-oxabicyclo[2,2,1]hept-2Z-ene, 7-oxabicyclo[2,2,1]heptane, bicyclo[2,2,2]oct-2Z-ene or bicyclo[2,2,2]octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR, a 6,6-dimethyl-bicyclo[3,1,1]heptane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR or at the 5-position by the group C(R.sup.2).dbd.NR and at the 6-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group C(R.sup.2).dbd.NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group C(R.sup.2).dbd.NR, R.sup.1 is a 6-caboxyhex-2-enyl group or a modification thereof as defined herein, R.sup.
Type:
Grant
Filed:
February 12, 1982
Date of Patent:
June 24, 1986
Assignee:
National Research Development Corporation
Abstract: 7-Oxabicycloheptane substituted prostaglandin analogs are provided having the structural formula ##STR1## wherein A is O or S and R is CH.sub.2 OH, ##STR2## or CO.sub.2 H, and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
Abstract: 7-Oxabicycloheptane substituted oxa prostaglandin analogs are provided having the structural formula ##STR1## wherein R is OH, ##STR2## (wherein R.sup.3 is lower alkyl, aryl, arylalkyl or lower alkylamino), ##STR3## (wherein R.sup.4 and R.sup.5 are the same or different and can be H, alkyl, aryl or arylalkyl, and R.sup.6 is alkyl or O-alkyl); R.sup.1 is lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl; R.sup.2 is hydrogen or lower alkyl; A is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; n is 1 to 4, and m is 1 to 8, and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
Type:
Grant
Filed:
January 22, 1985
Date of Patent:
May 13, 1986
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Martin F. Haslanger, Ravi K. Varma, Steven E. Hall
Abstract: 7-Oxabicycloheptane substituted oxo prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl, alkali metal or trihydroxymethylaminomethane, R.sup.1 is lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, R.sup.2 is hydrogen or lower alkyl, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --, n is 1 to 4, and m is 1 to 8, and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.
Type:
Grant
Filed:
November 1, 1984
Date of Patent:
March 11, 1986
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Steven E. Hall, Martin F. Haslanger, Ravi K. Varma
Abstract: 7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula ##STR1## wherein p is 0 to 4; A is CH.dbd.CH, (CH.sub.2).sub.2, or a single bond; m is 0 to 8; R is H, lower alkyl, alkali metal or tris(hydroxymethyl)aminomethane; n is 1 to 4; n' is 0, 1 or 2; q is 1 to 12; X is ##STR2## wherein R.sup.2 and R.sup.3 may be the same or different and are H or lower alkyl; t is 0 to 5; and R.sup.1 is H, lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, and including all stereoisomers thereof.The compounds are cardiovascular agents and antiinflammatory agents useful, for example, in the treatment of thrombolytic disease, inflammation and pain.
Abstract: The invention relates to a process for the production of 7-oxabicyclo-(2,2,1)hept-5-ene derivatives by conversion of acrylic acid esters and furanes in the presence of catalytic quantities of a Lewis acid. By use of Lewis acid, the reaction time is greatly reduced with good results in terms of product purity by comparison with known processes. The reaction products are intermediates, e.g. in the production of N-substituted acrylic acid amides.
Abstract: 7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl or alkali metal, R.sup.1 is lower alkyl, arylalkyl, aryl, cycloalkyl or cycloalkylalkyl, X is O, S or NH, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2, p is 0 to 4, n is 1 to 4, n' is 0 to 2, q is 1 to 4 and m is 0 to 8, and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease; and are antiinflammatory agents useful, for example, in the treatment of rheumatoid arthritis.
Abstract: The invention provides a process for preparing a 7-oxabicyclo[2.2.1]heptan-2-ol, which comprises treating a liquid-phase mixture of the corresponding cyclohex-3-en-1-ol, an aldehyde containing at least two carbon atoms and a suitable solvent, with oxygen in the presence of a catalyst which is soluble in the reaction mixture and which comprises a praseodymium compound and at least one compound selected from compounds of molybdenum, niobium, tantalum, tungsten, uranium and vanadium.
Abstract: Compounds of the formula ##STR1## wherein X is (--CR.sub.4 R.sub.4 --).sub.m in which m is 0 or 1;Y is (--CR.sub.5 R.sub.6 --).sub.n in which n is 0, 1 or 2;Z is (--CR.sub.7 R.sub.7 --).sub.p in which p is 1, 2 or 3;the sum of m+n+p is an integer of 2 to 5, inclusive;R.sub.2 and R.sub.3 each is H or alkyl, and the like;R.sub.1 is H or alkyl; andW is an unsaturated moiety, are useful as plant growth regulators and herbicides. Novel intermediates are also disclosed.
Type:
Grant
Filed:
June 25, 1984
Date of Patent:
November 19, 1985
Assignee:
Shell Oil Company
Inventors:
George B. Payne, Samuel B. Soloway, James E. Powell, Steven A. Roman, Willy D. Kollmeyer
Abstract: 7-Oxabicycloheptane substituted ether prostaglandin analogs are provided having the structural formula ##STR1## wherein A is O or ##STR2## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted oxo prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl, alkali metal or tris(hydroxymethyl)aminomethane, R.sup.1 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --, y is 0 to 4, m is 0 to 8, and n is 1 to 4, p is 1 to 12 and q is 0 to 5, and including all stereoisomers thereof.The compounds are antiinflammatory agents useful, for example, in the treatment of inflammatory diseases and analgesic agents as well as cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted prostaglandin alcohols are provided having the structural formula ##STR1## wherein A is --CH.dbd.CH--(CH.sub.2).sub.n -- or (CH.sub.2).sub.q ; B is a single bond or --CH.dbd.CH--; n is 1 to 5; q is 1 to 6; Q is --CH.dbd.CH-- or (CH.sub.2).sub.2 ; and R is lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl or lower alkenyl, with the proviso that when B is --CH.dbd.CH--, n is 1 to 3 or q is 1 to 4 and when B is a single bond, n is 1 to 5 or q is 1 to 6, and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane and 7-oxabicycloheptene prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Type:
Grant
Filed:
May 17, 1982
Date of Patent:
August 27, 1985
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
David L. Snitman, Martin F. Haslanger, Peter W. Sprague
Abstract: A compound of the formula ##STR1## wherein each R is H or alkyl and W is an optionally substituted unsaturated, cycloalkyl, secondary alkyl, aromatic or heterocyclic group, are useful as plant growth regulators and herbicides. The corresponding 6-oxabicyclo[3.2.1]octan-4-ols and 6-oxabicyclo[3.2.1]-octan-4-ones are novel intermediates.
Abstract: 7-Oxabicycloheptane substituted interphenylene prostaglandin ethers are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted enaminone prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted oxo prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl, alkali metal or tris(hydroxymethyl)aminomethane, R.sup.1 and R.sup.2 may be the same or different and are hydrogen or lower alkyl, R.sup.3 is hydrogen, lower alkyl, aryl or cycloalkyl, A is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --, m is 1 to 8, and n is 1 to 4, p is 1 to 12 and q is 0 to 5, and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted oxamide prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted thiocarbamate prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane ethers of prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted interphenylene prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: Mixtures containing 1,8-cineole are treated with hydroquinone to complex with and precipitate the 1,8-cineole. The complex in a crystalline form is separated from the mixture and dissociated to give 1,8-cineole which may be isolated in high-purity form by filtration or distillation.
Abstract: Fluoroaliphatic-thio,-sulfinyl and -sulfonyl substituted bicycloaliphatic amic acid amine salts of the formula: ##STR1## where R.sub.f is perfluoroalkyl, R' is alkylene optionally interrupted by --O--, --S-- or ##STR2## where R.sub.a is hydrogen or alkyl, Y is lower alkylene or --O--, n is 0-2, R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, hydroxy lower alkyl or together with the nitrogen to which they are attached, represented morpholino, R.sub.3, R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, or hydroxy lower alkyl, R.sub.6 is lower alkyl, carboxy lower alkyl, sulfo lower alkyl, hydroxy lower alkyl, benzyl or together with R.sub.5 and the nitrogen to which they are attached represent morpholino, and R is hydrogen or methyl are provided. These salts applied in the form of aqueous solutions, dispersions or emulsions are useful in rendering cellulosic and natural and synthetic polyamide materials oil and water repellent.
Type:
Grant
Filed:
June 13, 1983
Date of Patent:
May 7, 1985
Assignee:
Ciba Geigy Corporation
Inventors:
Jurgen Kaschig, Eduard K. Kleiner, Karl F. Mueller, Thomas W. Cooke
Abstract: 7-Oxabicycloheptane ethers of prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes are prepared by treating the corresponding cis-epoxycyclohexanol with acid in an inert solvent or by treating a 3-cyclohexen-1-ol which will produce the corresponding cis-epoxy alcohol successively or concurrently with an oxidizing agent and an acid in an inert solvent.
Abstract: A compound of the formula ##STR1## wherein each R is H or alkyl and W is an optionally substituted unsaturated, cycloalkyl, secondary alkyl, aromatic or heterocyclic group, are useful as plant growth regulators and herbicides. The corresponding 6-oxabicyclo[3.2.1]octan-4-ols and 6-oxabicyclo[3.2.1]octan-4-ones are novel intermediates.
Abstract: Optically active 7-oxabicycloheptane prostaglandin intermediates are provided having the general structure ##STR1## wherein one of R.sup.1 and R.sup.2 is --COOH, ##STR2## or --CH.sub.2 OH and the other is ##STR3## A method for preparing the above intermediates is also provided.
Abstract: 7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl or alkali metal, R.sup.1 is lower alkyl, arylalkyl, aryl, cycloalkyl or cycloalkylalkyl. A is --CH.dbd.CH or --(CH.sub.2).sub.2, n is 1 to 4, n' is 0 to 2 and m is 1 to 8, and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicyclo substituted prostaglandin phenyl carboxylic acid derivatives are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted carbamate prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane and prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane substituted amino prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Type:
Grant
Filed:
October 25, 1982
Date of Patent:
June 26, 1984
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Masami Nakane, David L. Snitman, Joyce Reid, Martin F. Haslanger
Abstract: 7-Oxabicycloheptane substituted amino prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Type:
Grant
Filed:
December 27, 1982
Date of Patent:
June 26, 1984
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Martin F. YHaslanger, Masami Nakane, Steven E. Hall
Abstract: 7-Oxabicycloheptane substituted amino prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Abstract: 7-Oxabicycloheptane hydrazone prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. pa The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Type:
Grant
Filed:
May 3, 1982
Date of Patent:
November 29, 1983
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Masami Nakane, Joyce Reid, Martin F. Haslanger
Abstract: 7-Oxabicycloheptane substituted amino prostaglandin analogs are provided having the structural formula ##STR1## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease.
Type:
Grant
Filed:
May 17, 1982
Date of Patent:
November 22, 1983
Assignee:
E. R. Squibb & Sons, Inc.
Inventors:
Masami Nakane, David L. Snitman, Joyce Reid, Martin F. Haslanger
Abstract: Novel alcohols of the formula ##STR1## where R.sup.5 is hydrogen are useful intermediates in the preparation of insecticidal esters. The insecticides are compounds in which R.sup.5 is a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a chlorophenyl-2-methylpropylcarbonyl group.
Abstract: A method of separating 1,4 cineole from a mixture containing 1,4 and 1,8 cineoles wherein the mixture is contacted with a zeolite having a constraint index of from 0.2 to 12 and having port sizes of approximately 6.7-7.0 angstroms. This causes the 1,4 cineole to be sorbed into the zeolite while the 1,8 cineole is excluded. The zeolite is then separated from the 1,8 cineole so that the 1,4 cineole may be desorbed from the zeolite. This desorbtion may be accomplished by heating the zeolite to a temperature above the boiling point of the cineole or by liquid phase displacement.