Two Rings Only Patents (Class 562/500)
  • Patent number: 4431669
    Abstract: There is disclosed certain cyclopropyl substituted polyenes useful for treating dermatoses such as acne, psoriasis and epithelial cancers.
    Type: Grant
    Filed: December 17, 1982
    Date of Patent: February 14, 1984
    Assignee: Schering Corporation
    Inventor: John J. Wright
  • Patent number: 4429148
    Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: January 31, 1984
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei Lai Chen
  • Patent number: 4425359
    Abstract: Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-16(S,R)-fluoro-PGF.sub.2.alpha.. The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.
    Type: Grant
    Filed: August 14, 1981
    Date of Patent: January 10, 1984
    Assignee: Farmitalia Carlo Erba
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4423066
    Abstract: A pentafluorobenzyl 2,2-dimethyl-3-vinylcyclopropane carboxylate of the formula ##STR1## in which R is hydrogen or halogen, andR.sup.1 is optionally substituted phenyl, orR and R.sup.1 together constitute an alkylene chain with at least two carbon atoms,which possess arthropodicidal properties.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: December 27, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4415756
    Abstract: New bicyclo[2.2.2]oct-5-en-2-ones of the formulae Ia and Ib in the form of pure enantiomers and processes for preparing them are described. The compounds are used for the preparation of pure enantiomers of the formula V by sensitized photoreaction or of compounds of the formula VI by unsensitized photoreaction.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: November 15, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Martin Demuth, Kurt Schaffner
  • Patent number: 4409398
    Abstract: (1R,cis)-Oxyimino-substituted cyclopropanecarboxylic acids are prepared via a (1R,4R,5S)-4-acetoxy-6,6-dimethyl-2-oxo-3-oxabicyclo [3.1.0]hexane intermediate.
    Type: Grant
    Filed: August 13, 1981
    Date of Patent: October 11, 1983
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4401601
    Abstract: A process for the preparation of tetrasubstituted cyclopropane compounds of the formula ##STR1## wherein Y is selected from the group consisting of --CN and --COOR, R is selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are individually selected from alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 together with the carbon atoms to which they are attached form a carbon homocycle of 3 to 6 carbon atoms with the 2 substituents not forming the ring being alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 on the one hand and R.sub.3 and R.sub.4 on the other together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms which are useful intermediates for the preparation of insecticidal esters and novel intermediates.
    Type: Grant
    Filed: March 23, 1981
    Date of Patent: August 30, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4389413
    Abstract: The 9,11-methano-13-aza-11a-carbathrombanoic acid analogues of the general formula: ##STR1## [wherein A represents ##STR2## (in which m is an integer of 1 to 6, the double bond between the carbon atoms in positions 5 and 6 in (iv) is in cis or trans-configuration or a mixture thereof and the phenylene group in (iv) represents o-, m- or p-phenylene), R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group of 1 to 12 carbon atoms, two R.sup.2 both represent hydrogen atoms or methyl groups, R.sup.3 represents a hydrogen atom or a hydroxy group, R.sup.4 represents a single bond or a straight- or branched-chain alkylene group of 1 to 5 carbon atoms, R.sup.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: June 21, 1983
    Inventors: Nobuyuki Hamanaka, Shinsuke Hashimoto, Masaki Hayashi
  • Patent number: 4386103
    Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: May 31, 1983
    Assignee: Merck & Co., Inc.
    Inventors: Stefano A. Pogany, Takeru Higuchi
  • Patent number: 4375557
    Abstract: Novel compounds of the formula I ##STR1## in which each of Y.sup.1 and Y.sup.2 independently represents a fluorine, chlorine or bromine atom and each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or an alkyl group having up to 10 carbon atoms, or R.sup.1 and R.sup.2 together represent an alkylene group having from 2 to 5 carbon atoms, may be converted by the action of base into the corresponding dihalovinylcyclopropane carboxylic acids.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: March 1, 1983
    Assignee: Shell Oil Company
    Inventor: Petrus A. Kramer
  • Patent number: 4370488
    Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.
    Type: Grant
    Filed: June 18, 1981
    Date of Patent: January 25, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4365085
    Abstract: The present invention relates to novel bicyclic compounds useful as photographic silver halide developing agents, to the preparation of these compounds and to photographic products, processes and compositions employing the same. The subject compounds may be represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, the same or different, each represents hydrogen, a hydrocarbon moiety, preferably an alkyl group, --COOH or --COOR.sup.1 wherein R.sup.1 is an alkyl group; R.sub.3 and R.sub.4, the same or different, each represent hydrogen or an alkyl group, R.sub.5 represents hydrogen or --COR.sup.2 wherein R.sup.2 is an alkyl group; R.sub.6 represents hydrogen when R.sub.5 is hydrogen and represents hydrogen or --OCOR.sup.3 wherein R.sup.3 is an alkyl group the same as R.sup.2 when R.sub.5 represents --COR.sup.2 ; X represents --OH, --NH.sub.2 or --NHCOR.sup.4 wherein R.sup.4 represents an alkyl group the same as R.sup.2 ; Y represents --OH or --OCOR.sup.5 wherein R.sup.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: December 21, 1982
    Assignee: Polaroid Corporation
    Inventors: James R. Bartels-Keith, Eva R. Karger
  • Patent number: 4363926
    Abstract: A bissilylated 1-hydroxycyclopropanecarboxylic acid of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently is a hydrogen atom or an alkyl radical, and additionally R.sup.2 and R.sup.3 can together form a 3- to 5-membered carbon bridge, andR.sup.5, R.sup.6 and R.sup.7 each independently is an alkyl radical, is produced by oxidizing with oxygen a cyclobutene-1,2-diol-bis-trialkyl-silyl ether of the formula ##STR2## The products, without isolation, may directly be hydrolyzed to remove the silyl radicals and form known intermediates for further reaction.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: December 14, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Hans-Joachim Knops, Uwe Priesnitz
  • Patent number: 4361577
    Abstract: .omega.-Nor-cycloalkyl-13,14-dehydro-prostaglandin compounds, specifically 5c-9-oxo-11.alpha.,15S-dihydroxy-20,19,18-tirnor-17-cyclohexyl-prost-5-en- 13-ynoic acid, the esters and salts thereof, having antiulcer and luteolytic activity, are disclosed.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: November 30, 1982
    Assignee: Carlo Erba - S.p.A.
    Inventors: Carmelo Gandolfi, Renato Pellegata, Roberto Ceserani, Maria M. Usardi
  • Patent number: 4351846
    Abstract: 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: Grant
    Filed: May 8, 1981
    Date of Patent: September 28, 1982
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Kimiichiro Matsumoto, Hajimu Miyake, Hisashi Suga
  • Patent number: 4351949
    Abstract: New organopalladium reactions involving the addition of pi-allylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation, and are specific inhibitors of thromboxane synthetase.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: September 28, 1982
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4349690
    Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.
    Type: Grant
    Filed: April 23, 1981
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4347379
    Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4334091
    Abstract: This invention relates to new compositions particularly suited for producing insecticidal intermediates.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: June 8, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Robert J. Tedeschi
  • Patent number: 4324902
    Abstract: 7-[5-oxo-3-hydroxy-2-(3-substituted)-3-hydroxypropyl)-1-cyclopentene]-hepta noic acids having the following general formula ##STR1## wherein X is oxygen or hydroxyl, R.sub.1 and R.sub.3 are independently hydrogen or methyl, and R.sub.2 is --(CH.sub.2)n-Y where n is an integer from 0 through 4 inclusive, and Y is phenyl, or a cycloalkyl group having 4 to 6 carbon atoms. Said acids as well as certain derivatives thereof are useful as nasal decongestants, inhibitors of gastric secretion, inhibitors of platelet aggregation, blood additives, smooth muscle stimulators, hypotensive agents, labor inducers, and in controlling ovulation.
    Type: Grant
    Filed: April 16, 1981
    Date of Patent: April 13, 1982
    Assignee: G. D. Searle & Co.
    Inventors: Masateru Miyano, Clifford R. Dorn
  • Patent number: 4320143
    Abstract: Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-13-14-dehydro-16(S,R)-fluoro-PGF.sub.2.alpha ..The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: March 16, 1982
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4312994
    Abstract: .alpha. Diene 16-hydroxy prostanoic acid derivatives displaying valuable pharmacological properties, e.g., gastric antisecretory, are described herein.
    Type: Grant
    Filed: March 25, 1981
    Date of Patent: January 26, 1982
    Assignee: G. D. Searle & Co.
    Inventor: Paul W. Collins
  • Patent number: 4308396
    Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an --OH group.
    Type: Grant
    Filed: March 12, 1979
    Date of Patent: December 29, 1981
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Ronald L. Magolda
  • Patent number: 4299967
    Abstract: There is described a new process for the preparation of optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3 position, and derivatives thereof. A racemate of certain cyclobutanones is reacted with a sulfurous acid salt of an optically active base to obtain a mixture of diastereomeric 4-2-(2',2',2'-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts; this mixture is then separated into the pure diastereomeric sulfonic acid salts. Either the pure diastereomeric sulfonic acid salts are converted directly to the desired optically active products, or the optically active cyclobutanones obtained from the pure diastereomeric sulfonic acids salts by decomposition is converted, in the presence of a base to the desired product. Optionally, the product, optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids can be converted to their 1',2'-dibromo derivatives.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: November 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: John G. Dingwall, Hans Greuter, Pierre Martin, Peter Ackermann, Laurenz Gsell
  • Patent number: 4297366
    Abstract: 2,2-Dimethyl-3-(2-fluoroalkyl-2-oxy-vinyl)-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is fluoroalkyl,R.sup.2 is an optionally substituted alkyl, cycloalkyl, aralkyl or aryl radical, andR.sup.3 is a radical customary in the alcohol component of pyrethroidswhich possess arthropodicidal properties. New intermediates therefor are also shown.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: October 27, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
  • Patent number: 4296121
    Abstract: What is disclosed are compounds of the formula ##STR1## which are structurally related to natural prostaglandins and a process for their manufacture. The compounds have valuable pharamacological properties and, therefore, they can be used as medicaments.
    Type: Grant
    Filed: August 2, 1979
    Date of Patent: October 20, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch, Elmar Konz
  • Patent number: 4284646
    Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C--or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.
    Type: Grant
    Filed: August 24, 1979
    Date of Patent: August 18, 1981
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
  • Patent number: 4283550
    Abstract: 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: Grant
    Filed: September 27, 1979
    Date of Patent: August 11, 1981
    Assignee: American Cyanamid
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4282249
    Abstract: (1R,cis)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andR.sup.1 is hydrogen, or certain optionally halogenated hydrocarbyl groups,are highly active pesticides or intermediates therefore.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: August 4, 1981
    Assignee: Shell Oil Company
    Inventors: Steven A. Roman, Samuel B. Soloway
  • Patent number: 4281153
    Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.
    Type: Grant
    Filed: January 17, 1980
    Date of Patent: July 28, 1981
    Assignee: American Cyanamid
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei Lai Chen
  • Patent number: 4281183
    Abstract: New cyclopropane compounds have the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andW is thienyl, furfuryl, --CO.sub.2 R.sup.1, --CONR.sup.1 R.sup.2, --SO.sub.3 R.sup.1, --SO.sub.2 NR.sup.1 R.sup.2, --PO.sub.3 H, --PO(OR.sup.1).sub.2, --NO.sub.2, --CN, --OR.sup.1, --SR.sup.1, --S(O)R.sup.1, --S(O).sub.2 R.sup.1, --NR.sup.1 R.sup.2, --N(O)R.sup.1 R.sup.2, or --(OCH.sub.2 CH.sub.2).sub.q --OR.sup.1 in which R.sup.1 and R.sup.2 are H or certain optionally-substituted hydrocarbyl groups, q is 1-4, p is 1 or 2 and when p is 1 then W.sup.1 is alkyl or when p is 2 then W.sup.1 is H. The compounds are pesticides or intermediates therefore.
    Type: Grant
    Filed: June 5, 1980
    Date of Patent: July 28, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4278688
    Abstract: Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-virylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing 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.sup.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: July 14, 1981
    Assignee: Ono Pharmaceutical Co.
    Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai
  • Patent number: 4275224
    Abstract: Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## such that a bicycloalkyl or bicycloalkenyl compound is formed, wherein m and n are integers having a value from 0 to 3, p is an integer having a value from 0 to 4 and q is an integer having a value of from 1 to 4 and wherein the double bond of such bicycloalkenyl is in the m, n, p, or q bridge; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: June 23, 1981
    Assignee: Miles Laboratories, Inc.
    Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
  • Patent number: 4275075
    Abstract: The present invention relates to prostaglandin analogues of the general formula: ##STR1## [wherein A represents a grouping of the formula: ##STR2## X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents a group of the formula --COOR.sup.4, in which R.sup.4 represents hydrogen or straight- or branched-chain alkyl of 1 to 12 carbon atoms, or a group of the formula --CH.sub.2 OR.sup.5, in which R.sup.5 represents hydrogen or alkylcarbonyl of 2 to 5 carbon atoms and R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent hydrogen, straight- or branched-chain alkyl of 1 to 12 carbon atoms, or an aryl group unsubstituted or substituted by one, two or three substituents selected from alkyl, alkoxy, alkylthio, monoalkylamino and dialkylamino groups and halogen atoms, the alkyl groups or moieties of the said groups containing from 1 to 5 carbon atoms in a straight- or branched-chain, with the proviso that at least one of the symbols R.sup.1, R.sup.
    Type: Grant
    Filed: June 14, 1978
    Date of Patent: June 23, 1981
    Assignee: ONO Pharmaceutical Co. Ltd.
    Inventors: Masayasu Kurono, Hisao Nakai, Shigeru Sakuyama
  • Patent number: 4273784
    Abstract: The present invention concerns prostaglandins having a cyclopropane ring in the 2,3 position.
    Type: Grant
    Filed: March 28, 1979
    Date of Patent: June 16, 1981
    Assignee: Sandoz Ltd.
    Inventor: Pietro Bollinger
  • Patent number: 4267361
    Abstract: 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: Grant
    Filed: September 27, 1979
    Date of Patent: May 12, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4260806
    Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula: ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an --OH group.The thromboxane analogues are potent thrombotic agents, useful in cardiovascular treatment.
    Type: Grant
    Filed: October 24, 1979
    Date of Patent: April 7, 1981
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
  • Patent number: 4260805
    Abstract: 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: Grant
    Filed: September 27, 1979
    Date of Patent: April 7, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4259523
    Abstract: This invention provides new mono-deuterated prostaglandins having prolonged uterotonic activity.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: March 31, 1981
    Assignee: Sandoz Ltd.
    Inventors: Pietro Bollingen, Manfred Krieger
  • Patent number: 4258207
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4254278
    Abstract: 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: Grant
    Filed: September 27, 1979
    Date of Patent: March 3, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4254277
    Abstract: (1R, Trans)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andR.sup.1 is certain optionally halogenated hydrocarbyl groups, are highly active pesticides or intermediates therefore.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: March 3, 1981
    Assignee: Shell Oil Company
    Inventors: Steven A. Roman, Samuel B. Soloway
  • Patent number: 4245121
    Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: January 13, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
  • Patent number: 4243677
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: January 6, 1981
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4243678
    Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: January 6, 1981
    Assignee: Byk Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Walter Krastinat
  • Patent number: 4242278
    Abstract: A process for the preparation of 2-(2',2',2',-trihalogenoethyl)-4-halogenocyclobutan-1-ones of the formula ##STR1## in which one of the radicals R.sub.1 and R.sub.2 is methyl and the other is hydrogen or methyl, or R.sub.1 and R.sub.2 together are an alkylene group having 2 to 4 carbon atoms, and X and Y are each chlorine or bromine, comprising reacting a 2,4,4,4-tetrahalogenobutyric acid chloride in the presence of an organic base with an ethylene compound which is disubstituted in 1-position by the radicals R.sub.1 and R.sub.
    Type: Grant
    Filed: October 3, 1978
    Date of Patent: December 30, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Hans Greuter, Eginhard Steiner, Daniel Bellus
  • Patent number: 4242521
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a hydrocarbyl group, W is a chlorine or bromine atom or --OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: January 25, 1980
    Date of Patent: December 30, 1980
    Assignee: Shell Oil Company
    Inventor: James E. Powell
  • Patent number: 4236027
    Abstract: This disclosure describes certain 11-alkoxy-9-keto- (or hydroxy)-prostenoic acid derivatives useful as anti-microbial agents, hypotensive agents, anti-ulcer agents, or as intermediates.
    Type: Grant
    Filed: October 17, 1977
    Date of Patent: November 25, 1980
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss
  • Patent number: 4223155
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an optionally halo-substituted hydrocarbyl group, and X is --C(O)Cl, --C(O)Br or C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the neutral terpene, 3-carene.
    Type: Grant
    Filed: July 26, 1979
    Date of Patent: September 16, 1980
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4220795
    Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: September 2, 1980
    Assignee: Miles Laboratories, Inc.
    Inventors: Harold C. Kluender, Henry C. Arndt