Oxy In Acid Moiety Patents (Class 560/53)
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Patent number: 4262134Abstract: The present invention provides novel 11-deoxy-11-hydroxymethyl-inter-phenylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 14, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4262136Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene4,5,6-trinor-3-oxa-11-deoxy-11-hy droxymethy-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 14, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4262133Abstract: The present invention provides novel 13,14-didehydro-interphenylene-11-deoxy-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 14, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4262135Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-19-oxo-PGE.su b.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 14, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260794Abstract: The present invention provides novel 11-deoxy-inter-phenylene-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260797Abstract: The present invention provides novel 9-deoxy-9-methylene-11-deoxy-11-hydroxymethyl-inter-phenylene-19-oxo-PGF.s ub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260789Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-11-deoxy-11-hydroxymethyl-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260783Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-13,14-dihydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 26, 1979Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260792Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-19-oxo-PGF.su b.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260786Abstract: The present invention provides novel 13,14-didehydro-interphenylene-11-deoxy-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260805Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: April 7, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4260796Abstract: The present invention provides novel inter-phenylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260800Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-9-de oxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260798Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-9-deoxy-9-met hylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260785Abstract: The present invention provides novel 13,14-didehydro-interphenylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260793Abstract: The present invention provides novel 9-deoxy-9-methylene-inter-phenylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260791Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-11-deoxy-9-deoxy-9-methylene-19-oxo-PGF.su b.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260799Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-11-h ydroxymethyl-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260787Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260784Abstract: The present invention provides novel 9-deoxy-9-methylene-11-deoxy-inter-phenylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260790Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-11-deoxy-11-hydroxymethyl-9-deoxy-9-methyl ene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260795Abstract: The present invention provides novel inter-phenylene-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260801Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-19-o xo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4260788Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: April 7, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4259250Abstract: The present invention provides novel thromboxane analogs and intermediates. Particularly, the present invention provides novel 11a-homo-PG intermediates for preparing 11a-methano TXA.sub.2 compounds.Type: GrantFiled: January 28, 1980Date of Patent: March 31, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4259523Abstract: This invention provides new mono-deuterated prostaglandins having prolonged uterotonic activity.Type: GrantFiled: May 11, 1979Date of Patent: March 31, 1981Assignee: Sandoz Ltd.Inventors: Pietro Bollingen, Manfred Krieger
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Patent number: 4254275Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: March 3, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4250321Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: February 10, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4250323Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: February 10, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4249021Abstract: Substituted 1-oxo-2,2-disubstituted-5-indanacetic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity.Type: GrantFiled: February 26, 1979Date of Patent: February 3, 1981Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
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Patent number: 4249016Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.Type: GrantFiled: March 7, 1977Date of Patent: February 3, 1981Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4247715Abstract: Indanyloxy compounds having 2-alkynyl substituents which exhibit diuretic, saluretic, and uricosuric activity are described. The compounds are obtained according to a process involving selective etherification of a 5-hydroxyindanone followed by alkynylation with a silylated alkynyl bromide to provide novel silylated intermediates which are hydrolyzed to indanyloxy compounds such as (6,7-dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acid.Type: GrantFiled: April 9, 1979Date of Patent: January 27, 1981Assignee: Mead Johnson & CompanyInventors: Porter C. Johnson, William L. Matier
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Patent number: 4247709Abstract: The present invention relates to a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one and to certain compounds for use in that process.British Pat. Spec. No. 1,474,377 discloses inter alia that 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one possesses useful anti-inflammatory activity. A particularly favored process has now been discovered that can be used to produce 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl) butan-2-one in particularly good yield.The present invention provides a process for the preparation of 4-(6.sup.1 -methoxy-2.sup.1 -naphthyl)butan-2-one which process comprises the hydrogenation of a compound of the formula (I): ##STR1## wherein Ar is a 6-methoxy-2-naphthyl group; X and Y are each hydrogen atoms or together represent a second bond between the carbon atoms to which they are attached; and R is a group such that --CO.sub.2 R represents an ester group convertible by hydrogenation to a CO.sub.2 H group.Type: GrantFiled: December 26, 1978Date of Patent: January 27, 1981Assignee: Beecham Group LimitedInventors: Carl J. Rose, David Miller
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Patent number: 4243611Abstract: Prostaglandin derivatives having a 19,20-didehydro, a 19-hydroxy, or a 19-keto feature are disclosed, including processes for preparing them and the appropriate intermediates.A typical 19-hydroxy compound of this invention is 19-hydroxy-19-methyl-PGF.sub.2.alpha.Type: GrantFiled: April 2, 1979Date of Patent: January 6, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4238414Abstract: The present invention relates to novel 2-decarboxy-2-aminomethyl-6a-carba-PGI.sub.2 compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.Type: GrantFiled: September 27, 1979Date of Patent: December 9, 1980Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4238623Abstract: Disclosed are prostaglandin analogues having the structural formula, ##STR1## in which: T is selected from the group consisting of carboxyl, alkoxycarbonyl or cyano;M is selected from the group consisting of carbonyl, R-hydroxymethylene or S-hydroxymethylene;L is selected from the group consisting of methylene or methine, provided L is methine only if J is methine;J is selected from the group consisting of methylene, ethylene, R-hydroxymethylene, S-hydroxymethylene or methine, provided J is methine only if L is methine;W is selected from the group consisting of ##STR2## T.sub.1 and T.sub.2 are attached to adjacent carbon atoms; T.sub.1 is selected from the group consisting of hydrogen or phenyl, provided T.sub.1 is phenyl only if T.sub.2 is lower alkyl;T.sub.2 is selected from the group consisting of n-pentyl or lower alkyl, provided T.sub.2 is lower alkyl only if T.sub.1 is phenyl; orT.sub.1 and T.sub.2 are joined together to form an alkylene group of 4 or 6 carbon atoms.Type: GrantFiled: March 29, 1976Date of Patent: December 9, 1980Assignee: Miles Laboratories, Inc.Inventor: Robert T. Buckler
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Patent number: 4238492Abstract: Arylcarbonylphenoxyalkylcarboxylic acids, and alkyl esters and salts thereof, are described. The compounds may be formulated into therapeutic compositions and administered to animals, including humans, for the treament of hyperlipidaemia and related diseases.Type: GrantFiled: May 24, 1979Date of Patent: December 9, 1980Assignee: Societe de Recherches Industrielles S.O.R.I.Inventor: Bernard Majoie
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Patent number: 4237305Abstract: Substituted phenylacetic acid compounds represented by the following general formula and preparation thereof: ##STR1## wherein R.sup.1 is hydrogen or protected carboxy,R.sup.2 is hydrogen, or protected amino, provided that when R.sup.1 is hydrogen, then R.sup.2 is protected amino, and when R.sup.2 is hydrogen, then R.sup.1 is protected carboxy,R.sup.3 is oxo, hydroxyimino or protected hydroxyimino,R.sup.4 is hydrogen or halogen, andm is an integer of 1 to 3.Type: GrantFiled: March 30, 1977Date of Patent: December 2, 1980Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Masashi Hashimoto, Osamu Nakaguti, Teruo Oku, Hidekazu Takeno
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Patent number: 4233298Abstract: This invention is concerned with esters of p-carbonylphenoxy-isobutyric acids of the general formulae: ##STR1## wherein R is a phenyl group substituted by one or two halogen atoms;R' is H, CH.sub.3, C.sub.6 H.sub.5, SCH.sub.3, OCH.sub.3, or, SO.sub.2 CH.sub.3 ;R" is CH.sub.3 or C.sub.2 H.sub.5 ;Y is C.sub.1 -C.sub.4 alkoxy, phenoxy, phenoxy substituted by one or two halogen atoms, or, OCH.sub.2 O--CO--C(CH.sub.3).sub.3 ;Z is C.sub.1 -C.sub.4 alkyl, phenyl or R;NR.sub.1 R.sub.2 is N(CH.sub.3).sub.2 N(C.sub.2 H.sub.5).sub.2, morpholino, piperidino, hexamethylenimino, pyrrolidino.This invention is also concerned with acid addition salts obtained from formula Ia compounds with acids.Compounds of formulae I and Ia are useful as hypocholesterolemiant and hypolipidemiant agents.Type: GrantFiled: September 1, 1977Date of Patent: November 11, 1980Assignee: Orchimed SAInventor: Andre Mieville
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Patent number: 4233454Abstract: The disclosure relates to a novel sequence of reactions for manufacturing known prostaglandin intermediates, and to novel chemical intermediates obtained in the course of the novel reaction sequence, for example methyl 5.beta.-chloro-2.beta.-dimethoxymethyl-3.alpha.-hydroxycyclopent-1.alpha.- ylacetate.Type: GrantFiled: September 10, 1979Date of Patent: November 11, 1980Assignee: Imperial Chemical Industries LimitedInventor: Keith B. Mallion
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Patent number: 4229585Abstract: 16-fluoro-substituted prostaglandin analogs of the formula: ##STR1## in which R is hydrogen, a C.sub.1 -C.sub.12 alkyl group or a cation of a pharmaceutically acceptable base; one of R.sub.1 and R.sub.2 is hydrogen and the other is hydroxy or acyloxy or R.sub.1 and R.sub.2 take together, form a oxo group; one of R.sub.4 and R.sub.5 is hydroxy and the other is hydrogen; R.sub.6 is hydrogen, methyl or fluorine; n is zero or an integer of 1 to 6; and R.sub.7 is phenyl or phenyl substituted by at least one of halogen C.sub.1 -C.sub.6 alkoxy or trihalomethyl.Type: GrantFiled: April 27, 1979Date of Patent: October 21, 1980Assignee: Farmitalia Carlo ErbaInventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4226985Abstract: 11-Substituted prostaglandins E.sub.1, E.sub.2 and F.sub.2.alpha. useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy and a process for preparing these prostaglandins.Type: GrantFiled: April 2, 1979Date of Patent: October 7, 1980Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4227015Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.Type: GrantFiled: February 14, 1979Date of Patent: October 7, 1980Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
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Patent number: 4223157Abstract: Prostaglandin E (PGE)-type derivatives and analogs having a 6-ketone feature are disclosed, including processes for preparing them and the appropriate intermediates, said derivatives having pharmacological activity.Type: GrantFiled: August 27, 1979Date of Patent: September 16, 1980Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4220605Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.Type: GrantFiled: December 23, 1977Date of Patent: September 2, 1980Assignees: Director General of Agency of Industrial Science and Technology, Sanko Chemical Co. Ltd., Nippon Soda Co. Ltd.Inventor: Juichi Imamura
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Patent number: 4219662Abstract: This invention comprises 11-deoxy-17-phenyl-18,19,20-trinor-prostaglandin-type compounds which exhibit prostaglandin-type pharmacological activity, such as lowering blood pressure, inhibiting gastric secretion, regulating the reproductive cycle, and the like.Type: GrantFiled: February 28, 1977Date of Patent: August 26, 1980Assignee: The Upjohn CompanyInventors: Gordon L. Bundy, Norman A. Nelson
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Patent number: 4218378Abstract: The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.Type: GrantFiled: May 1, 1979Date of Patent: August 19, 1980Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4216336Abstract: Prostaglandin F.sub.1 .alpha. (PGF.sub.1 .alpha.) derivatives having a 5-keto feature, for example ##STR1## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.Type: GrantFiled: June 22, 1979Date of Patent: August 5, 1980Assignee: The Upjohn CompanyInventor: Roy A. Johnson
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Patent number: 4216172Abstract: A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid.Type: GrantFiled: March 13, 1978Date of Patent: August 5, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4215142Abstract: Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-vinylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aralkyl group containing from 7 to 12 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 6 carbon atoms, a phenyl group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group, alkyl group containing from 1 to 4 carbon atoms or phenyl group, a --C.sub.m H.sub.2m COOR.sup.5 group (wherein m represents an integer of from 1 to 12 and R.sup.5 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.6 group (wherein R.sup.6 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n represents an integer of from 2 to 12), or a ##STR2## group (wherein R.sup.7 and R.Type: GrantFiled: September 8, 1978Date of Patent: July 29, 1980Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai