Oxy In Acid Moiety Patents (Class 560/53)
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Patent number: 4582913Abstract: Disclosed are novel 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having the formula ##STR1## with X.sub.2 or SO.sub.2 X.sub.2 wherein X is Cl or Br.Type: GrantFiled: June 11, 1984Date of Patent: April 15, 1986Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4582914Abstract: This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-halo-3(S)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.Type: GrantFiled: January 31, 1985Date of Patent: April 15, 1986Assignee: Merck & Co., Inc.Inventors: Ralph P. Volante, Thomas R. Verhoeven, Meyer Sletzinger, James M. McNamara, Thomas M. H. Liu, Edward G. Corley
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Patent number: 4578505Abstract: This invention relates to novel allenic prostanoic acid derivatives having the following formula ##STR1## wherein R is hydrogen; or straight or branched chain alkyl of 1 to 6 carbon atoms, inclusivewherein R.sub.1 is hydrogen; or straight or branched chain alkyl of 1 to 6 carbon atoms, inclusive; or vinyl (--CH.dbd.CH.sub.2)wherein R.sub.2 is straight or branched chain alkyl of 1 to 6 carbon atoms; or cycloalkyl group containing 3 to 6 carbon atoms; or phenyl; or phenoxywherein R.sub.3 is hydrogen; or straight chain alkyl of 1 to 3 carbon atomswherein m is an integer of from 1 to 4, inclusive,wherein n is an integer of from 1 to 3, inclusive with the proviso that the sum of m and n does not exceed 5,wherein y is an integer of from 1 to 3.These compounds are useful by reason of their gastric antisecretory and cytoprotective activity.Type: GrantFiled: September 4, 1984Date of Patent: March 25, 1986Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Richard M. Weier
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Patent number: 4571428Abstract: 6-Substituted-4-hydroxy-tetrahydropyran-2-ones, useful as anti-atherosclerotic agents, are obtainable by the process of the invention. The 6-substituents have a phenyl, naphthyl, tetrahydronaphthyl or indolyl nucleus bound through an ethenyl unit. The invention includes novel intermediates.Type: GrantFiled: July 8, 1983Date of Patent: February 18, 1986Assignee: Sandoz, Inc.Inventor: Prasad K. Kapa
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Patent number: 4565818Abstract: A 6- and/or 7-oxy-trans-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline in which the 3-position is substituted by an optionally amidated carboxy group, an optionally etherified hydroxymethyl group, a cyanomethyl group, an alkyl- or aryl-thiomethyl group or a sulfamoylamino or carbamoylamino group, or a physiologically-hydrolysable and -acceptable ester thereof. The subject compounds are useful as pharmaceuticals, in particular as prolactin secretion inhibitors, dopaminergic agents ad dopamine receptor stimulating agents.Type: GrantFiled: October 14, 1982Date of Patent: January 21, 1986Assignee: Sandoz Ltd.Inventors: Rene Nordmann, Trevor J. Petcher
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Patent number: 4564696Abstract: Process for the production of 4-alkoxyacetoacetic acid esters from 4-chloro or 4-bromoacetoacetic acid esters. 4-chloro or 4-bromoacetoacetic acid ester is reacted with more than one equivalent of an alkali alcoholate in an aprotic solvent effectively at a temperature of 50.degree. to 100.degree. C.Type: GrantFiled: September 27, 1982Date of Patent: January 14, 1986Assignee: Lonza Ltd.Inventor: Claudio Abacherli
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Patent number: 4562204Abstract: Trans-.DELTA..sup.2 -prostaglandin D derivatives of the formula: ##STR1## wherein [A] is a group of the formula: ##STR2## X is ethylene or cis-vinylene, C.sub.13 -C.sub.14 -C.sub.15 is: (i) a group of the formula: ##STR3## when [A] is a group of the formula (II) or (III), or (ii) a group of the formula: ##STR4## when [A] is a group of the formula (IV), R is hydrogen or alkyl, R.sup.1 is a single bond or alkylene, R.sup.2 is alkyl, cycloalkyl, phenyl or phenoxy, the double bonds between C.sub.2 -C.sub.3 and between C.sub.13 -C.sub.14 are both E, the double bond between C.sub.9 -C.sub.10 is Z and the double bonds between C.sub.12 -C.sub.13 and between C.sub.14 -C.sub.15 are E, Z or a mixture thereof, provided that when R.sup.1 is a single bond, R.sup.2 does not represent a substituted or unsubstituted phenoxy group, and cyclodextrin clathrates and non-toxic salts thereof, possess anti-tumor activity.Type: GrantFiled: June 28, 1983Date of Patent: December 31, 1985Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hirohisa Wakatsuka, Takashi Yamato, Shinsuke Hashimoto
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Patent number: 4562068Abstract: This invention relates to a topical cosmetic preparation for treating oily hair or seborrhea which contains a sebosuppressively effective amount of at least one 4-aryl-4-oxo-but-2-enoic acid derivative.Type: GrantFiled: January 18, 1983Date of Patent: December 31, 1985Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hinrich Moller, Siegfried Wallat
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Patent number: 4560403Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: September 22, 1983Date of Patent: December 24, 1985Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4551264Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.Type: GrantFiled: March 14, 1983Date of Patent: November 5, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Michael Romer, Georg Weber
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Patent number: 4550190Abstract: Naphthalenyloxy carboxylic acids of the formula ##STR1## wherein X, R, m and n are as hereinafter set forth, are described. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A), which renders them useful as agents for the treatment of allergic conditions.Type: GrantFiled: March 21, 1983Date of Patent: October 29, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Ronald A. LeMahieu
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Patent number: 4547584Abstract: Novel 3-hydroxy-4-alkyloxyphenyl benzoates compounds particularly well suited as sweeteners in foodstuff.Type: GrantFiled: December 29, 1983Date of Patent: October 15, 1985Assignee: General Foods CorporationInventors: Jed A. Riemer, Paul R. Zanno, Ronald E. Barnett
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Patent number: 4544771Abstract: Halogenobiphenyl derivatives of Formula I ##STR1## wherein R.sup.1 and R.sup.2 are each alkyl or alkoxy in each case of 1-10 C atoms, Cy is 1,4-cyclohexylene, Ph is 1,4-phenylene, Q is --O--Cy-- or --O--Ph--, m and n are each 0 or 1 and X is F, Cl or Br, can be used as components of liquid crystal dielectrics for electrooptical display elements.Type: GrantFiled: February 8, 1985Date of Patent: October 1, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Michael Romer, Joachim Krause, Georg Weber
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Patent number: 4540808Abstract: Process for the production of 4-alkoxyacetoacetic acid esters from 4-chloro- or 4-bromoacetoacetic esters. The 4-chloro- or 4-bromoacetoacetic ester is reacted with a highly concentrated solution of an alkali alcoholate in alcohol having been concentrated at elevated temperatures, at temperatures of 50.degree. to 120.degree. C. At least 2.8 mole of the alkali alcoholate are used per mole of 4-chloro- or 4-bromoacetoacetic ester.Type: GrantFiled: September 27, 1982Date of Patent: September 10, 1985Assignee: Lonza, Ltd.Inventor: Erich Greth
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Patent number: 4539419Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or lower alkyl, X is hydrogen or halogen, and A is the group ##STR2## wherein R.sub.1 is hydrogen, acyl or lower alkyl, R.sub.2 is hydrogen or lower alkyl, m is an integer from 2 to 4, n is an integer from 1 to 3, and t is an integer from 1 to 5, provided that R.sub.1 is adjacent to --(CH.sub.2).sub.m [O(CH.sub.2).sub.m ].sub.n O--, and, when R.sub.2 is hydrogen, salts thereof with pharmaceutically acceptable bases, are described. The compounds of formula I are useful as agents for the treatment of allergic conditions.Type: GrantFiled: May 2, 1983Date of Patent: September 3, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Ronald A. LeMahieu
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Patent number: 4537984Abstract: A process for producing a 2-(4-hydroxyphenoxy) propionate derivative represented by the formula: ##STR1## where Alk is a C.sub.1 -C.sub.5 alkyl group, which comprises reacting a phenoxy propionate derivative represented by the formula: ##STR2## where Alk is as defined above, with a peroxide to obtain a formate derivative represented by the formula: ##STR3## where Alk is as defined above, and hydrolyzing the formate of the formula III.Type: GrantFiled: April 26, 1984Date of Patent: August 27, 1985Assignee: Nissan Chemical Industries Ltd.Inventors: Isao Hashiba, Tadashi Nishikimi, Shuji Tsuchiya
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Patent number: 4536592Abstract: The present invention encompasses 16-alkyl, 16-hydroxy-2-substituted prostaglandins which exhibit cytoprotective and antisecretory activity with greatly reduced diarrhea side effects.Type: GrantFiled: February 16, 1984Date of Patent: August 20, 1985Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki, Richard M. Weier
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Patent number: 4535183Abstract: This invention is directed to novel ether compounds of formula (I) ##STR1## which are of value in medicine in the palliation of haemoglobinopathies, in particular sickle-cell anemia, and also in the palliation of pulmonary dyefunction, protection from the effects of hypoxia and the radio-sensitization of tumours. The invention is also directed to methods for the preparation of the ether compounds, to pharmaceutical formulations containing them, the preparation of such formulations and the use of the compounds in human medicine. Also provided by the invention are intermediates of value in the preparation of the ether compounds, by the methods described, and the preparation of the intermediates.Type: GrantFiled: December 18, 1981Date of Patent: August 13, 1985Assignee: Burroughs Wellcome Co.Inventor: Geoffrey Kneen
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Patent number: 4533732Abstract: This invention relates to derivatives of 3-propionylsalicylic acid represented by the formula (1) ##STR1## wherein R represents a hydrogen atom, a lower alkyl group or a group ##STR2## (wherein R.sup.1 and R.sup.2 represent a lower alkyl group or R.sup.1 and R.sup.2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a hydrogen atom or a halogen atom, R being the group ##STR3## when X is a hydrogen atom. This invention also relates to processes for preparing the same.Type: GrantFiled: September 30, 1983Date of Patent: August 6, 1985Assignees: Yamamoto Chemical Industrial Company, Limited, Osaka Municipal GovernmentInventors: Hiroshige Inoue, Kenichi Fukushima, Ikuzo Nishiguchi
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Patent number: 4518784Abstract: There is presented a process for the manufacture of hexahydronaphthacene derivatives of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydrogen atom or a hydroxy group of R.sup.1 and R.sup.2 together represent a protected oxo group, R.sup.3 represents a hydrogen atom or a hydroxy or acyloxy group and R.sup.4 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group or ##STR3## in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group.Also presented are certain of the novel derivatives per se and various novel intermediates in the process.Type: GrantFiled: February 23, 1984Date of Patent: May 21, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Broadhurst, Cedric H. Hassall, Gareth J. Thomas
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Patent number: 4518612Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.Type: GrantFiled: December 21, 1983Date of Patent: May 21, 1985Assignee: Fisons plcInventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
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Patent number: 4517202Abstract: Prostaglandin analogues of the general formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group, Y.sup.1 represents a carbonyl or hydroxymethylene group, represents a single or double bond, A.sup.1 represents an alkylene linkage containing 2 or 3 carbon atoms and optionally bearing a methyl or ethyl substituent, R.sup.2 represents a hydrogen atom or a methyl or ethyl group and R.sup.3 represents a hydrogen atom or else R.sup.2 and R.sup.3 form an alkylene linkage containing 2 or 3 carbon atoms, optionally bearing a methyl or ethyl substituent, such that the symbols A.sup.1, R.sup.2 and R.sup.3, together with the carbon atoms through which they are connected, form a cycloalkyl ring of 6, 7 or 8 carbon atoms, optionally bearing one or two methyl or ethyl substituents, X.sup.1 represents an ethylene or trans-vinylene group, Y.sup.2 represents a carbonyl or hydroxymethylene group, and either (i) A.sup.Type: GrantFiled: May 26, 1983Date of Patent: May 14, 1985Assignee: May & Baker LimitedInventors: Clive W. Bird, Helene I. Butler, Michael P. L. Caton, Edward C. J. Coffee, Geoffrey Darnbrough, Terance W. Hart
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Patent number: 4507498Abstract: Phenoxycarboxylic acids of the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, Z and n are as hereinafter set forth, are as described. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A), which renders them useful as agents for the treatment of allergic conditions.Type: GrantFiled: January 24, 1983Date of Patent: March 26, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
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Patent number: 4500731Abstract: A compound of the formula I: ##STR1## in which R.sub.1 and R.sub.2 in any position on the benzene ring are different from each other, and independently represent a hydroxy group or an alkoxy group containing from 1 to 8 carbon atoms, or else R.sub.1 and R.sub.2 together form an --OCH.sub.2 CH.sub.2 O-radical, and R represents a hydrogen atom or an alkyl group containing from 1 to 8 carbon atoms, as well as the alkali metal, alkaline earth metal, ammonium or amine salts of the said products of formula I in which R represents a hydrogen atom. These compounds have been found useful in the treatment of hyperchlorhydria, gastric and gastro-duodenal ulcers, gastritis, hiatal hernias, and gastric and gastro-duodenal ailments accompanied by gastric hyperacidity. Pharmaceutical compositions including these compounds are disclosed along with methods for their production.Type: GrantFiled: October 20, 1982Date of Patent: February 19, 1985Assignee: Roussel UclafInventors: Mario Bianchi, Fernando Barzaghi
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Patent number: 4500544Abstract: Ascochlorin derivatives of the formula: ##STR1## wherein R is a hydroxyl group, a lower alkoxy group, a pyridyl group, an amino group, a dialkylamino group, a phenoxyalkyl group which may have a substituent in the nucleus, or a phenyl group which may have a substituent in the nucleus; and n is an integer of 0 to 5, a process for preparing the same and a pharmaceutical composition containing the same are disclosed.The derivatives are useful to treat diabetes, improve lipid metabolism and control tumors.Type: GrantFiled: August 27, 1982Date of Patent: February 19, 1985Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Tomoyoshi Hosokawa, Ikutoshi Matsuura, Hidenori Takahashi, Kunio Ando, Gakuzo Tamura
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Patent number: 4499295Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.Type: GrantFiled: May 9, 1983Date of Patent: February 12, 1985Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4499299Abstract: Compounds which antagonize the slow-reacting substance of anaphylaxis or components thereof, e.g., leukotrienes, in warm blooded animals as well as intermediates and methods for their preparation, pharmaceutical compositions and methods for their administration. The compounds are diphenyl carboxylic acids with particular linking groups between the individual phenyl rings and the carboxylic acid moiety. Particular utilities are to relieve asthma and inflammation in man.Type: GrantFiled: December 6, 1982Date of Patent: February 12, 1985Assignee: ICI Americas Inc.Inventors: Peter R. Bernstein, Alvin K. Willard
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Patent number: 4495370Abstract: A process for the preparation of a 5-aryloxy-1-chloro-3,3-dimethyl-2-pentanone of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is halogen, alkyl having 1 to 4 carbon atoms, alkoxy or alkylthio each having 1 to 2 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each having 1 to 2 carbon atoms and 1 to 5 halogen atoms, cyclohexyl, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, nitro, cyano, alkoxy-carbonyl having 1 to 4 carbon atoms in the alkyl moiety, phenyl or halophenyl, m and n each independently is an integer from 0 to 5, and m+n.ltoreq.5,comprising reacting 1,1,5-trichloro-3,3-dimethyl-1-pentene of the formula ##STR2## with a phenol of the formula ##STR3## in the presence of a base in a diluent, to produce a compound of the formula ##STR4## and subjecting such reaction product to acid hydrolysis.Type: GrantFiled: May 27, 1983Date of Patent: January 22, 1985Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4477679Abstract: A process is disclosed for the production of alkyl-5-substituted-3-furoate compounds of the general formula: ##STR1## in which R.sub.1 is an unsubstituted or substituted aryl which substituent will not affect the reaction, such as phenyl and R.sub.2 is a lower alkyl having 1 to 6 carbon atoms employing alkyl-4-oxo-5-substituted-pentanoate as a starting material.Type: GrantFiled: March 1, 1983Date of Patent: October 16, 1984Assignee: CPC International Inc.Inventors: David V. Petrocine, John A. Swidinsky
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Patent number: 4465850Abstract: The invention relates to the treatment and prevention of injury to the gray matter of the brain and to the spinal chord due to accidents, ischemic stroke, cardiac arrest, arrested breathing, Reye's syndrome and hydrocephalus by the administration of (indanyloxy)butanoic acids, their derivatives, analogs and salts thereof.Type: GrantFiled: September 30, 1982Date of Patent: August 14, 1984Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4458091Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 30, 1982Date of Patent: July 3, 1984Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4456768Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions 4,4; 7,7; 10,10; and 5.Type: GrantFiled: May 1, 1981Date of Patent: June 26, 1984Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4450292Abstract: A compound of the formula (I) ##STR1## in which the three methoxy radicals are in the 3,4,5, or 2,4,6 or 2,4,5 or 2,3,5 or 2,3,6 positions, in which either A and B together represent a double bond or else A represents a hydrogen atom and B represents a hydroxy radical, and in which R represents a hydrogen atom or an alkyl containing 1 to 5 carbon atoms, in the various possible stereoisomeric forms, as well as the alkali metal, alkaline-earth metal, or amine salts thereof in which R represents a hydrogen atom, methods of producing the same, pharmaceutical compositions containing the same and treatment of various gastric ailments are disclosed.Type: GrantFiled: April 14, 1982Date of Patent: May 22, 1984Assignee: Roussel UclafInventors: Yani Christidis, Robert Fournex
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Patent number: 4440943Abstract: 3,7-Substituted phenoxiodinin-5-ium compounds are effective against a variety of aerobic and anaerobic bacteria as well as fungi. The compounds of this invention may be prepared by the direct iodination of a suitably substituted diphenyl ether with iodosyl sulfate in concentrated sulfuric acid. The resulting bisulfate anion may be exchanged with a desired anion by standard metathetic processes.Type: GrantFiled: March 15, 1982Date of Patent: April 3, 1984Assignee: The Dow Chemical CompanyInventor: Edward E. Flagg
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Patent number: 4421927Abstract: The present invention relates to a new cinnamoyl-cinnamic acid derivative selected from the group constituted by:(i) the m-cinnamoyl-cinnamic acid derivatives of formula ##STR1## in which: X.sub.o,X.sub.1,X.sub.2,X.sub.3,X.sub.4, which are identical or different, each represent an atom of hydrogen, a halogen, a lower alkyl group, a lower alkoxy group, the group NRR' (where R and R' identical or different, each represent an atom of hydrogen or a lower alkyl group), the group NO.sub.2, CF.sub.3 or OH;R.sub.1 represents an atom of hydrogen or a lower alkyl group;R.sub.2 represents an atom of hydrogen or the methyl group;Y represents a group OH, OR.sub.3 (where R.sub.3 is a lower alkyl group), NRR' (where R and R' are defined as hereinabove) or the group O(CH.sub.2).sub.n NR.sub.4 R.sub.5 (where n is an integer of value 1 to 5--and preferably 2 or 3)--; and R.sub.4 and R.sub.Type: GrantFiled: October 22, 1981Date of Patent: December 20, 1983Assignee: Societe de Recherches Industrielles (S.O.R.I.)Inventor: Francois Picart
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Patent number: 4412958Abstract: 5-Phenyl-2S-pentanol is synthesized stereospecifically from S ethyl lactate. The method provides easily purified 5-phenyl-2S-pentanol useful in the synthesis of central nervous system active (CNS) agents such as levonantradol.Type: GrantFiled: August 5, 1982Date of Patent: November 1, 1983Assignee: Pfizer Inc.Inventors: Berkeley W. Cue, Jr., Bernard S. Moore
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Patent number: 4410720Abstract: 11-Unsubstituted 16-fluoro-prostaglandin E.sub.2 useful as blood pressure lowering agents.Type: GrantFiled: October 26, 1981Date of Patent: October 18, 1983Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4410537Abstract: This invention is directed to novel ether compounds of formula (I) ##STR1## which are of value in medicine in the palliation of haemoglobinopathies, in particular sickle-cell anaemia, and also in the palliation of pulmonary dysfunction, protection from the effects of hypoxia and the radio-sensitization of tumors. The invention is also directed to methods for the preparation of the ether compounds, to pharmaceutical formulations containing them, the preparation of such formulations and the use of the compounds in human medicine. Also provided by the invention are intermediates of value in the preparation of the ether compounds, by the methods described, and the preparation of the intermediates.Type: GrantFiled: June 9, 1981Date of Patent: October 18, 1983Assignee: Burroughts Wellcome Co.Inventor: Geoffrey Kneen
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Patent number: 4407757Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.Type: GrantFiled: December 31, 1980Date of Patent: October 4, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
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Patent number: 4406909Abstract: A fungicidally active 4-substituted-1-azolyl-1-phenoxy-3,3-dimethyl-butan-2-one or -ol of the formula ##STR1## in which A is a nitrogen atom or CH,B is --CO-- or CH(OH),R is cyano or X--R.sup.1,R.sup.1 is alkyl, optionally substituted aryl or optionally substituted aralkyl,X is oxygen, sulphur, SO or SO.sub.2,Z each independently is halogen, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulphonyl, nitro, cyano, alkoxycarbonyl or optionally substituted phenyl, andn is 0, 1, 2 or 3,or an addition product thereof with a physiologically acceptable acid or with a metal salt. Intermediates therefor of the formula ##STR2## are also new.Type: GrantFiled: May 19, 1981Date of Patent: September 27, 1983Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Hans-Ludwig Elbe, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger
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Patent number: 4403100Abstract: The present invention provides novel (11R)-11-deoxy-11-alkyl-6-oxo-prostaglandins which are useful for curing and preventing duodenal ulcers and for preventing or treating gastrointestinal cell damage caused by the use of other pharmacological agents.Type: GrantFiled: October 30, 1981Date of Patent: September 6, 1983Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4365075Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.Type: GrantFiled: December 30, 1976Date of Patent: December 21, 1982Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4365077Abstract: 11-Desoxy-16-aryloxy-.omega.-tetranorprostaglandins are disclosed. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins but they exhibit a greater tissue specificity of action.Type: GrantFiled: February 22, 1979Date of Patent: December 21, 1982Assignee: Pfizer Inc.Inventors: Jasjit S. Bindra, James F. Eggler, Michael R. Johnson, Thomas K. Schaaf
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Patent number: 4359581Abstract: A process for preparing a 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester of the formula ##STR1## wherein R.sub.1 is alkyl of 1-6 carbon atoms or phenalkyl of 7-10 carbon atoms andR.sub.2 is hydrogen, alkyl or 1-6 carbon atoms, phenalkyl of 7-10 carbon atoms, tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, tri-C.sub.1-4 -alkylsilyl, wherein the alkyl moieties can optionally be substituted by phenyl, or ##STR2## wherein R.sub.3 is alkyl of 1-6 carbon atoms or aryl of 6-12 carbon atoms, comprises oxidizing the corresponding 7-hydroxy-2-oxabicyclo [3,3,0]octan-3-ylideneacetic acid ester of the formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, to form the corresponding ketone, reacting the latter with a base which opens the ether oxygen containing ring, and then reducing the resultant product to prepare the 3-oxo-7-hydroxy-bicyclo[3,3,0]octan-2-ylcarboxylic acid ester.Type: GrantFiled: June 5, 1981Date of Patent: November 16, 1982Assignee: Schering AGInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen
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Patent number: 4356314Abstract: The invention relates to novel [(5,6,9a-substituted-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]alkanoi c and cycloalkanoic acids, and their analogs, esters, salts and derivatives. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful in the treatment and prevention of injury to the brain and spinal chord due to accidents, ischemic stroke and hydrocephalus; compositions for such uses are also disclosed.Type: GrantFiled: February 19, 1981Date of Patent: October 26, 1982Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Gerald E. Stokker, Norman P. Gould
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Patent number: 4356187Abstract: Novel esters of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN, R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, halogen, alkenyl of 2 to 3 carbon atoms and alkyl of 1 to 3 carbon atoms, Y' is selected from the group consisting of ##STR2## R.sub.4 ' and R.sub.5 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, fluorine, bromine, chlorine and R.sub.4 ' and R.sub.Type: GrantFiled: April 17, 1980Date of Patent: October 26, 1982Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4356313Abstract: The invention relates to novel [(5,6,9a-substituted-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]alkanoi c and cycloalkanoic acids and their analogs, esters, salts and derivatives. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful in the treatment and prevention of injury to the brain and spinal chord due to accidents, ischemic stroke and hydrocephalus; compositions for such uses are also disclosed.Type: GrantFiled: February 19, 1981Date of Patent: October 26, 1982Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Gerald E. Stokker, Norman P. Gould
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Patent number: 4351846Abstract: Prostaglandin analogues of the formula: ##STR1## [wherein R.sup.1 represents hydrogen or alkyl of 1 to 12 carbon atoms, R.sup.2 represents a single bond or alkylene of from 1 to 5 carbon atoms, R.sup.3 represents hydrogen, alkyl or alkoxy of 1 to 8 carbon atoms, cycloalkyl or cycloalkyloxy of 4 to 7 carbon atoms unsubstituted or substituted by alkyl of 1 to 8 carbon atoms, or phenyl or phenoxy unsubstituted or substituted by halogen, trifluoromethyl or alkyl of 1 to 4 carbon atoms, one of R.sup.4 and R.sup.5 represents hydrogen and the other represents hydroxy or R.sup.4 and R.sup.5 together represent oxo, R.sup.6 represents hydrogen or a hydroxy-protecting group which may be removed under acidic conditions, the double bond between the carbon atoms in positions 13 and 14 is trans, the wavy line attached to the carbon atom in position 15 represents .alpha.- or .beta.- configuration or a mixture thereof and, when one of R.sup.4 and R.sup.Type: GrantFiled: May 8, 1981Date of Patent: September 28, 1982Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Kimiichiro Matsumoto, Hajimu Miyake, Hisashi Suga