Plural Rings In Alcohol Moiety Patents (Class 560/107)
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Patent number: 4201869Abstract: A multi-step, stereospecific total synthesis of steroids is disclosed. The starting materials for this process are the relatively inexpensive and readily available m-alkoxy acetophenones. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly A-ring aromatic steroids. This process features an early optical resolution and a unique asymmetric induction which insures the correct stereochemistry of the final steroidal product.Type: GrantFiled: February 21, 1978Date of Patent: May 6, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Noal Cohen, Gabriel Saucy
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Patent number: 4197406Abstract: The present disclosure is concerned with 17a-(m-iodobenzoyloxy) substituted D-homosteroids and a process for their manufacture. The compounds are useful as intermediates and also as hormonal agents, particularly progestational agents.Type: GrantFiled: May 7, 1979Date of Patent: April 8, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Andor Furst, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
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Patent number: 4196215Abstract: Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologically acceptable metals salts thereof, have anti-inflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.Type: GrantFiled: June 28, 1978Date of Patent: April 1, 1980Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4195916Abstract: Novel liquid crystal compounds are disclosed, which are chiral esters based upon the phenol ##STR1## Typical examples are: ##STR2## and mixtures of these compounds have a helical pitch such that the mixtures reflect light of a specific wavelength when illuminated with ordinary light and the pitch is temperature sensitive so that the mixtures can be used in temperature indicating devices. Specific examples are given as are samples of mixtures that can be used in phase change electro-optic display devices.Type: GrantFiled: April 5, 1978Date of Patent: April 1, 1980Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, George W. Gray, Damien G. McDonnell
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Patent number: 4188495Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrollo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: November 14, 1977Date of Patent: February 12, 1980Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4188345Abstract: Fluorine-substituted vitamin D compounds, methods for preparation of such compounds and fluorinated intermediate compounds used in such methods are disclosed. The fluorine-substituted vitamin D compounds are characterized by vitamin D-like activity in stimulating intestinal calcium transport and bone mobilization and in promoting the calcification of rachitic bone.Type: GrantFiled: July 26, 1978Date of Patent: February 12, 1980Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Joseph L. Napoli, Jr., Bruce L. Onisko
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Patent number: 4181674Abstract: The stereospecific alkylation of a novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described using a range of lithium-, copper or magnesium-containing organometallic reagents. This reaction provides a 5-endo-protected hydroxyl-bicyclo[2,2,1]-heptan-2-one system from which prostaglandin compounds of the F series having a protecting group at the 9-position hydroxyl group may readily be obtained by a sequence of reactions.Type: GrantFiled: December 2, 1976Date of Patent: January 1, 1980Assignee: Allen & Hanburys LimitedInventors: Roger F. Newton, Stanley M. Roberts, David K. Rainey, Michael J. Dimsdale
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Patent number: 4178381Abstract: C-homoestratrienes of the formula ##STR1## wherein ##STR2## R.sub.1 and R.sub.2 are the same or different, and each is hydrogen, acyl, alkyl, cycloalkyl or tetrahydropyranyl; andR.sub.3 is hydrogen, ethynyl or chloroethynyl; possess very good estrogenic properties.Type: GrantFiled: December 4, 1978Date of Patent: December 11, 1979Assignee: Schering, AktiengesellschaftInventors: Gregor Haffer, Ulrich Eder, Gerhard Sauer, Rudolf Wiechert, Yukishige Nishino, Gunter Neef
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Patent number: 4176233Abstract: An optically active 4-(4-substituted-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone is reacted with a protonic acid to provide an optical isomer of a cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibe nzo[b,d]pyran-9-one. Reaction of said norpinanone with a Lewis acid provides an optical isomer of trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-di benzo[b,d]pyran-9-one. The optically active norpinanones are prepared by reaction of a 5-substituted-resorcinol with an optically active 6,6-dimethyl-2,4-diacetoxy-2-norpinene or an optically active 6,6-dimethyl-2,2-diacetoxy-3-norpinene, which compounds are derived from optically active .beta.-pinenes.Type: GrantFiled: April 21, 1978Date of Patent: November 27, 1979Assignee: Eli Lilly and CompanyInventors: Robert A. Archer, William A. Day
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Patent number: 4169145Abstract: .omega.-NOR-CYCLOALKYL-13,14-DEHYDRO-PROSTAGLANDIN COMPOUNDS, SPECIFICALLY 13,14-DEHYDRO-17-CYCLOHEXYL-20,19,18-TRINOR-PGF.sub.2.alpha. having antiulcer and luteolytic activity, are disclosed.Type: GrantFiled: September 21, 1977Date of Patent: September 25, 1979Assignee: Carlo Erba S.p.A.Inventors: Carmelo Gandolfi, Renato Pellegata, Roberto Ceserani, Maria M. Usardi
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Patent number: 4163016Abstract: 16-Substituted prostaglandins position and the 16-substituted-15-keto prostaglandins, said prostaglandins being useful as antisecretory agents, blood pressure lowering agents, anti-ulcerogenic agents and antihypertensive agents.Type: GrantFiled: July 5, 1977Date of Patent: July 31, 1979Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Perry Rosen
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Patent number: 4162988Abstract: Novel compounds exhibiting liquid crystal properties have the formula:R-.phi.-.phi.-X-.phi.-R1,whereinR and R1 are, independently in each case, hydrogen or an alkyl, aryl, alkylaryl, arylalkyl, or alkoxy group containing from 1 to about 12 carbon atoms, a halogen, a cyano group, an alkyl cyano group of from 1 to 5 carbon atoms, a --CF.sub.3 group, an --N.sub.3 group, a nitro group or a --N(CH.sub.3).sub.2 group, andX is ##STR1## These compounds are especially useful for increasing the clearing point and reducing the operating voltage of liquid crystal compositions including other ester or Schiff base liquid crystal compounds, and the like.Type: GrantFiled: March 6, 1978Date of Patent: July 31, 1979Assignee: Motorola, Inc.Inventors: Robert C. Maze, Everett P. Oppenheim, Reese M. Reynolds
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Patent number: 4159991Abstract: .alpha.-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R.sub.3 COOH and R.sub.4 COOH upon an .alpha.-acyloxymalononitrile, R.sub.1 COO--C(CN).sub.2 --R.sub.2, in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.Type: GrantFiled: August 22, 1977Date of Patent: July 3, 1979Assignee: Produits Chimiques Ugine KuhlmannInventors: Bernard Dubreux, Serve Y. Delavarenne, Jean-Pierre Schirmann
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Patent number: 4156694Abstract: The present invention relates to novel benzo(b) bicyclo[3.3.1]nones of the general formula I: ##STR1## and a salt or nitrogen oxide thereof, in which R.sub.1 and R.sub.2 stand for hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, an optionally substituted aralkyl group or an acyl group orR.sub.1 and R.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ringR.sub.3 is a free, etherified or esterified hydroxy,X and Y stand for hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 C-atoms, nitro, CF.sub.3 or an acyloxy group, having valuable biological activities, particularly anorectic activity.Type: GrantFiled: December 30, 1977Date of Patent: May 29, 1979Assignee: Akzona IncorporatedInventors: Colin L. Hewett, David S. Savage, James Redpath, Thomas Sleigh, Duncan R. Rae
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Patent number: 4155918Abstract: The present disclosure relates to novel D-homosteroids. More particularly, the invention is concerned with hormonally active novel D-homosteroids, a process for the manufacture thereof and pharmaceutical preparations containing same.Type: GrantFiled: March 16, 1978Date of Patent: May 22, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Andor Furst, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
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Patent number: 4147655Abstract: Novel mesomorphic substances, constituting, in certain temperature ranges, nematic or smectic liquid crystals, are compounds of the formula ##STR1## wherein Y is H or CN;R is alkyl or alkoxy of 1 to 10 carbon atoms;R' is alkyl of 1 to 10 carbon atoms or ##STR2## and X is Br, Cl or CN.Type: GrantFiled: January 9, 1978Date of Patent: April 3, 1979Assignee: Thomson-CSFInventors: Jean-Claude Dubois, Huu T. Nguyen, Annie Zann
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Patent number: 4147777Abstract: Pharmaceutically active compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom or a substituted or unsubstituted aliphatic or aromatic mono- or poly-carboxylic acid acyl radical and R.sub.5 represents a glycosyl group, are provided together with processes for their production and pharmaceutical compositions containing them. These compounds possess valuable cicatrizing and anti-inflammatory properties.Type: GrantFiled: March 17, 1977Date of Patent: April 3, 1979Assignee: Inverni Della Beffa S.p.A.Inventor: Giuseppe Mustich
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Patent number: 4146740Abstract: Intermediates useful for the synthesis of the valuable perfume material norpatchoulenol, said intermediates having the formula, for instance ##STR1## This intermediate, which is a novel compound, is useful as an intermediate for the production of ethers, esters and other intermediates, which are also novel compounds, such as, for instance, methyl, ethyl, isopropyl and benzyl ethers which can be represented by the formulae ##STR2## wherein R is hydrogen or lower carboxylic acyl. ##STR3## WHERE R is lower alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, benzyl, etc., and ##STR4## where ##STR5## is a lower acyl radical such as acetyl, propionyl, butyryl, benzoyl, etc. Such intermediates are readily prepared by etherification and esterification reaction procedures and said intermediates are useful as intermediates for the preparation of other odorants.Type: GrantFiled: February 10, 1977Date of Patent: March 27, 1979Assignee: Societe Anonyme Roure Bertrand DupontInventor: Paul J. Teisseire
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Patent number: 4139716Abstract: The present disclosure relates to D-homosteroids. More particularly, the disclosure is concerned with 19-nor-D-homopregnanes, a process for the manufacture thereof and pharmaceutical preparations containing same.Type: GrantFiled: March 25, 1976Date of Patent: February 13, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Andor Furst, Jurg A. W. Gutzwiller, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
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Patent number: 4138581Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-.alpha.-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.Type: GrantFiled: February 2, 1976Date of Patent: February 6, 1979Assignee: Sterling Drugs Inc.Inventors: Hiroaki Minatoya, Benjamin F. Tullar, Walter D. Conway
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Patent number: 4138497Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1 R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxylakylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.Type: GrantFiled: July 29, 1977Date of Patent: February 6, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
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Patent number: 4138359Abstract: A new and novel liquid crystal composition having broad temperature and chemical stability is disclosed. The liquid crystal composition comprises a compound having the general formula: ##STR1## wherein R represents an alkyl or alkoxyl group and X represents an alkyl, alkoxyl, nitro or cyano group. The method for making the liquid crystal compound includes the methylation of 4-phenyl-2-chlorophenol and like compounds.Type: GrantFiled: February 25, 1977Date of Patent: February 6, 1979Assignee: Citizen Watch Co., Ltd.Inventor: Yutaka Mizukuchi
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Patent number: 4137269Abstract: The present disclosure relates to steroids. More particularly, the disclosure is concerned with D-homosteroids, a process for the manufacture thereof and pharmaceutical preparations containing same. The subject D-homosteroids have high endocrinal activity and are particularly active as anti-inflammatory agents.Type: GrantFiled: October 12, 1976Date of Patent: January 30, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Andor Furst, Marcel Muller, Ulrich Kerb, Klaus Kieslich, Rudolf Wiechert
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Patent number: 4137417Abstract: Enamides are prepared by hydrogenating oximes having at least one hydrogen atom at the .alpha.-position in the presence of a carboxylic anhydride using a ruthenium catalyst. These enamides are important to obtain amino group-containing compounds by reduction or polymerization.Type: GrantFiled: April 26, 1977Date of Patent: January 30, 1979Assignee: Sumitomo Chemical Company, LimitedInventor: Motoo Hazama
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Patent number: 4134911Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]-heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo [2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.Type: GrantFiled: December 2, 1976Date of Patent: January 16, 1979Assignee: Allen & Hanburys LimitedInventor: Stanley M. Roberts
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Patent number: 4131655Abstract: D-homopregnanes of the formula ##STR1## wherein R.sup.6 is hydrogen, chloro, fluoro or methyl; X is .beta.-hydroxymethylene or carbonyl; R.sup.17a is hydroxy, lower alkanoyloxy or aroyloxy; R.sup.21 is hydrogen, chloro, fluoro, hydroxy, lower alkanoyloxy, aroyloxy, sulfate or phosphate; and the dotted line in the 1,2-position of the A-ring denotes an additional carbon-carbon bondAnd pharmaceutically acceptable salts thereof, processes for the preparation thereof and pharmaceutical compositions containing them as the active ingredient are disclosed. The D-homopregnanes of the present invention exhibit hormonal activity and are useful for the treatment of inflammation.Type: GrantFiled: April 20, 1978Date of Patent: December 26, 1978Assignee: Hoffman-La Roche Inc.Inventors: Leo Alig, Andor Furst, Marcel Muller, Ulrich Kerb, Rudolf Wiechert
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Patent number: 4129599Abstract: Method is provided for cyclization of polyunsaturated substituted acylic or monocarbocyclic initiator group containing compound having an endocyclic double bond with a chalcogen atom in the allylic position of the initiator group and having at least two sites of unconjugated aliphatic unsaturation in the side chain substituent on the ring. The polyunsaturated compound is cyclized in the presence of a strong acid in a protic solvent which is inert to the acid, preferably a hydroxylic solvent. Mild temperatures and varying times are employed. The products are useful primarily as intermediates for naturally occurring and synthetic steroids. By appropriate substitution of the side chain, the steroidial products are provided with the substituent at C-11, which upon cyclization results in the alpha-configuration. By resolution of the intermediates prior to cyclization, optically active steroids can be obtained.Type: GrantFiled: June 23, 1977Date of Patent: December 12, 1978Assignee: The Board of Trustees of Leland Stanford Jr. UniversityInventors: Sina Escher, Grant E. Dubois
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Patent number: 4123552Abstract: Fungus and mold growth in crops and organic matter are inhibited by the use of bis-carboxylic acid esters and compositions thereof. In a preferred embodiment, crops and animal feedstuffs are preserved during storage by applying a microbiocidal amount of a mono-, di or trioxymethylene, or lower alkylidene bis-alkanoate, or a mixture thereof.Type: GrantFiled: October 17, 1975Date of Patent: October 31, 1978Assignee: Chevron Research CompanyInventors: Daniel L. Kensler, Jr., Gustave K. Kohn, David D. Walgenbach
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Patent number: 4117234Abstract: Estrogenic steroids are synthesized by combining under conditions favoring the formation of a trans-olefin, a .gamma.-arylpropanal with a 5,5,8,8-tetraalkoxy Wittig reagent. After hydrolysis of the gem-diethers, the resulting dioxo is internally condensed to form a cyclopentenone. The ketone is reduced to an oxy group and the resulting 2-(6'-arylhex-3'-enyl-1)cyclopent-2-en-1-ol or derivative thereof is cyclized to the .DELTA..sup.13,17 -estrene, preferably 17-alkyl-.DELTA..sup.13,17 -estrene with the A ring aromatized. After epoxidation, the 17-alkyl derivative is rearranged to form the 13-alkyl-1,3,5(10)-estratien-17-one. New compounds are provided as intermediates and final products.Type: GrantFiled: September 24, 1976Date of Patent: September 26, 1978Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: William S. Johnson, Paul A. Bartlett
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Patent number: 4116981Abstract: There is provided a novel method of synthesizing certain tetracyclic quinones. In particular, there is provided a novel route to the synthesis of (+)-7-deoxydaunomycinone and analogs thereof which includes the provision of novel tetrahydronaphthoquinones and tetracyclic quinone intermediates. The compounds of the present invention are provided through a route comprising a Diels-Alder addition of certain isobenzofurans to certain novel tetrahydronaphthoquinones. The products of the synthetic route provided herein may be converted into compounds of known antibiotic and antineoplastic activity.Type: GrantFiled: May 2, 1977Date of Patent: September 26, 1978Assignees: Yuh-Geng Tsay, Research CorporationInventor: Andrew S. Kende
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Patent number: 4115456Abstract: Alkyne compounds of the formula ##STR1## wherein R.sup.1 is H, alkyl of up to 4 carbon atoms or phenyl; R.sup.2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R.sup.3 and R.sup.4 are H, F, Cl or Br and n is 0 or 1, and physiologicaly acceptable metals salts thereof, have antiinflammatory activity. These compounds can be made from compounds of the formula ##STR2## wherein Q is a functionally-modified hydroxy and R.sup.1, R.sup.3, R.sup.4 and n are as above by treatment with a solvolyzing agent.Type: GrantFiled: June 18, 1976Date of Patent: September 19, 1978Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4113972Abstract: 1,1-Diphenyl-2-hydroxy-3-aminopropane derivatives are useful for their psychotropic activity and, in particular are useful as antidepressants.Type: GrantFiled: June 21, 1976Date of Patent: September 12, 1978Assignee: Beecham Group LimitedInventor: Judith Ann Clark
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Patent number: 4105792Abstract: 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: May 25, 1976Date of Patent: August 8, 1978Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4104043Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: December 12, 1972Date of Patent: August 1, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4103025Abstract: Pharmaceutically active compounds of the formula ##STR1## wherein --OR.sub.1, --OR.sub.2, --OR.sub.3 and --OR.sub.4, which may be the same or different, each represents a free or esterified hydroxyl group and --COOR.sub.5 represents a free or esterified carboxyl group, are provided together with processes for their production and pharmaceutical compositions containing them. Compounds of formula II and III possess valuable cicatrizing and anti-inflammatory properties.Type: GrantFiled: March 17, 1977Date of Patent: July 25, 1978Assignee: Inverni Della Beffa S.p.A.Inventor: Giuseppe Mustich
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Patent number: 4097678Abstract: 3.alpha.-Hydroxy and 3.alpha.-acyloxy- .DELTA..sup.9(11) -5.alpha.-D-homo-20-ketopregnenes of the formula ##STR1## wherein R is hydrogen or acyl, R.sub.1 is hydrogen or methyl and R.sub.2 is methyl or ethyl, are produced by esterifying a corresponding 3.beta.-hydroxy-5.alpha.-20-keto pregnane of the formula ##STR2## wherein R.sub.1 and R.sub.2 have the values given above, with m-iodo-benzoic acid with inversion of the 3.beta.-oxy group to a 3.alpha.-oxy group; chlorinating the thus-produced 3.alpha.-m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3.alpha.-iodobenzoyl group is split off in a conventional manner to produce the corresponding 3.alpha.-hydroxy steroid and optionally the thus-produced 3.alpha.-hydroxy steroid is esterified to produce a desired 3-ester thereof.Type: GrantFiled: June 8, 1976Date of Patent: June 27, 1978Assignee: Schering AktiengesellschaftInventors: Ulrich Kerb, Rudolf Wiechert, Otto Engelfried
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Patent number: 4092483Abstract: A multi-step, stereospecific total synthesis of steroids is disclosed. The starting materials for this process are the relatively inexpensive and readily available m-alkoxy acetophenones. The process is suitable for the preparation of racemic or optically active, medicinally valuable steroids, particularly A-ring aromatic steroids. This process features an early optical resolution and a unique asymmetric induction which insures the correct stereochemistry of the final steroidal product.Type: GrantFiled: September 24, 1975Date of Patent: May 30, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Noal Cohen, Gabriel Saucy
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Patent number: 4091006Abstract: A new series of substituted esters of 3-hydroxyindone compounds have been found to have exceptional miticidal and herbicidal activity.Type: GrantFiled: October 1, 1975Date of Patent: May 23, 1978Assignee: Union Carbide CorporationInventors: John A. Durden, Jr., Anthony A. Sousa, John F. Stephen
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Patent number: 4088695Abstract: Cyclopentane derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen or a carboxylic acyl group, and either (I) R.sup.2 represents a group of the formula:--CR.sup.3 R.sup.4 R.sup.5 II(wherein R.sup.3 and R.sup.4 represent hydrogen or alkyl, and R.sup.5 represents hydrogen, or alkyl, alkoxy, cycloalkyl or adamantyl, or R.sup.5 represents alkyl substituted by alkoxy, or by cycloalkyl or by adamantyl, or the group --CR.sup.3 R.sup.4 R.sup.5 together forms a cycloalkyl or adamantyl group), X represents trans-vinylene or ethylene and Y represents carbonyl or a group of the formula: ##STR2## wherein R.sup.6 represents hydrogen or alkyl, and R.sup.7 represents hydrogen or a carboxylic acyl group, or else(ii) R.sup.2 represents a group of the formula:--A-Z-R.sup.8 IV(wherein A represents alkylene, Z represents a direct bond or oxygen or sulphur, and R.sup.Type: GrantFiled: January 23, 1975Date of Patent: May 9, 1978Assignee: May & Baker LimitedInventors: Michael P. L. Caton, Edward C. J. Coffee, Gordon L. Watkins
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Patent number: 4083997Abstract: 10-(2-substituted-aminoethyl)-10,11-dihydro-5-methylene-2 or 3 7 or 8-substituted or unsubstituted-5H-dibenzo[a,d]cycloheptenes e.g., 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cyclohe ptene, prepared by various methods including acid dehydration of the corresponding dibenzo[a,d]cycloheptene-5-ols. The compounds are useful as anti-depressants.Type: GrantFiled: September 1, 1976Date of Patent: April 11, 1978Assignee: Sandoz, Inc.Inventors: William J. Houlihan, Jeffrey Nadelson
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Patent number: 4077996Abstract: A process for the preparation of trans-decahydronaphthalene compounds of Formula I ##STR1## wherein X is lower alkyl, --(CH.sub.2).sub.3 --Z--R.sub.2, ##STR2## --(CH.sub.2).sub.3 COOR.sub.4, or --(CH.sub.2).sub.3 CN; Y and Z are ketalized carbonyl or free, esterified, or etherified hydroxymethylene;U is halogen;R.sub.1, r.sub.2, and R.sub.3 are lower alkyl; andR.sub.4 is alkyl;Wherein an octahydronaphthalene compound of Formula II ##STR3## is converted, in the presence of bases, by reaction of a trialkyl chlorosilane of the formula(R.sub.5).sub.3 Si--Clwherein the R.sub.5 each are lower alkyl group, to a hexahydronaphthalene compound of the formula ##STR4## The hexahydronaphthalene compound is hydrogenated, in an inert solvent with hydrogen in the presence of a platinum-, palladium-, or rhodium-containing hydrogenation catalyst, to an octahydronaphthalene compound of the formula ##STR5## and a vinyl ketone of the formulaXCOCH.dbd.CH.sub.Type: GrantFiled: April 14, 1976Date of Patent: March 7, 1978Assignee: Schering AktiengesellschaftInventors: Gerhard Sauer, Ulrich Eder, Gregor Haffer, Gunter Neef, Rudolf Wiechert
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Patent number: 4075241Abstract: The compounds 2-Aryl-3-amino-1-butanol derivatives of the formula ##STR1## wherein R represents hydrogen or acyl; R.sup.1 and R.sup.2 each independently represents hydrogen, phenyl lower alkyl, or lower alkoxy substituted phenyl lower alkyl, or both R.sup.1 and R.sup.2 are lower alkyl; and their pharmaceutically acceptable acid salts.The compounds are crystalline solids or liquids which, having two asymmetry centers, can be obtained in their stereoisomeric forms as racemic mixtures or in their optically active forms. The compounds have cardiovascular activity as coronary dilators.The compounds can be prepared by reacting an .alpha.-arylcrotonate with ammonia or with an amine followed by hydrogenation of the carbalkoxy group to give the corresponding butanol. The butanols are acylated in usual ways to give the compounds of formula (I) wherein R represents an acyl group.Type: GrantFiled: May 8, 1972Date of Patent: February 21, 1978Assignee: Gruppo Lepetit S.p.A.Inventors: Elvio Bellasio, Franco Cristiani
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Patent number: 4068082Abstract: Esters are prepared by reaction of acyl halides and alcohols or hydroxyalkyl esters and acid halides in the presence of a tertiary amine and polar aprotonic solvents. Bis(2-methacrylatoethyl) phthalate is prepared by the reaction of phthaloyl chloride with 2-hydroxyethyl methacrylate in pyridine and acetone. Bis-phenol-A-bis(2-methacrylatoethyl)ether is prepared from 2,2-bis[4-(2-hydroxyethoxy)phenyl]-propane and methacryl chloride in acetone.Type: GrantFiled: September 19, 1973Date of Patent: January 10, 1978Assignee: Lee PharmaceuticalsInventors: Donald G. Stoffey, Jan Alexander Orlowski
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Patent number: 4066685Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: April 10, 1975Date of Patent: January 3, 1978Assignee: SCM CorporationInventor: William Oroshnik
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Patent number: 4060633Abstract: Phenylalkanols of the formula ##STR1## wherein Ar is phenyl or phenyl monosubstituted or disubstituted by F, Cl, Br and/or CH.sub.3 ; X is F, Cl, Br or CN; m is 0 or 1; and n 2 or 3; possess antiinflammatory activity and can be produced by treating a compound of formula ##STR2## wherein Q is a functionally modified hydroxy group and Ar, X, m and n have the values given above, with a solvolyzing agent.Type: GrantFiled: April 28, 1976Date of Patent: November 29, 1977Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4058569Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: March 1, 1976Date of Patent: November 15, 1977Assignee: SCM CorporationInventor: William Oroshnik
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Patent number: 4052422Abstract: Novel 4,5-seco-steroids having anti-inflammatory activity are disclosed herein.Type: GrantFiled: November 8, 1974Date of Patent: October 4, 1977Assignee: E. R. Squibb & Sons, Inc.Inventor: Christopher M. Cimarusti
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Patent number: 4048195Abstract: Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula ##STR1## WHEREIN M IS AN INTEGER HAVING A VALUE OF 1 TO 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR.sub.2) and carbonyl; R.sub.8 when taken alone is hydrogen, R.sub.9 when taken alone is lower alkoxy-carbonyl, aryloxy-carbonyl, lower cycloalkyloxy-carbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R.sub.8 when taken alone is hydrogen; R.sub.9 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R.sub.Type: GrantFiled: July 14, 1976Date of Patent: September 13, 1977Assignee: Hoffmann-La Roche Inc.Inventor: Zoltan George Hajos
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Patent number: RE30241Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-alpha-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.Type: GrantFiled: June 20, 1977Date of Patent: March 25, 1980Assignee: Sterling Drug Inc.Inventors: Hiroaki Minatoya, Benjamin F. Tullar, Walter D. Conway