Cyclopentyl (e.g., Prostoglandins, Etc.) Patents (Class 562/503)
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Patent number: 5225439Abstract: The novel 13, 14-dihydro-15-keto prostaglandins E of the invention have remarkable preventive effects against ulcers. Further, the novel 13,14-dihydro-15-keto-prostaglandins E of the invention have an advatage that they have none of side effects which prostaglandin E intrinsically has, or can remarakably reduce such effects of the prostaglandin E. Therefore, the novel 13, 14-dihydro-15-keto prostaglandins E of the invention are effective for animal and human use for treatment and prevention of ulcers, such as duodenal ulcer and gastric ulcer.Type: GrantFiled: April 5, 1991Date of Patent: July 6, 1993Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5221763Abstract: The present invention provides new compounds, 13,14-dihydro-15-keto-PGFs, and vassopressors containing them, which raise blood pressure without substantial ephemeral depression of blood pressure, trachea or enteron contraction effect inherent in usual PGFs.Type: GrantFiled: September 16, 1992Date of Patent: June 22, 1993Assignee: R-Tech Ueno, Ltd.Inventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
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Patent number: 5221799Abstract: A compound of the formula: ##STR1## wherein L and M are hydrogen atom, hydroxy, lower alkyl, hydroxy(lower)alkyl or oxo, provided that at least one of L and M is not hydrogen atom and that the five-membered ring may have one or two double bonds,X.sub.1 and X.sub.2 are hydrogen atom, halogen atom or lower alkyl,Y is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CO--CH.sub.2 --,Z is --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--CH.sub.2 or --CH.sub.2 --CH.dbd.CH--,R is hydrogen atom, lower alkyl, lower cycloalkyl, monocyclic aryl, monocyclic aryl(lower)alkyl or monocyclic aroyl(lower)alkyl,R.sub.2 is single bond or lower alkylene,R.sub.Type: GrantFiled: July 30, 1992Date of Patent: June 22, 1993Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuji Ueno, Tomio Oda
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Patent number: 5214056Abstract: A 1,3,2-dioxathiolane oxide derivative is represented by the following formula: ##STR1## wherein X represents --S(O)-- or --S(O).sub.2 --;R.sup.1 represents a hydrogen atom, an alkali metal atom, a benzyl group, or a lower alkyl group;R.sup.2 represents a lower alkyl group which may be substituted with a methylthio group, or a benzyl group, andR.sup.3 and R.sup.4 may be the same or different and independently represent a hydrogen atom, an alkyl group having one to ten carbon atoms, a lower alkyl group substituted with a guanidyl group, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, a benzyl group, or a phenethyl group, or together form an alkylene group.Type: GrantFiled: August 20, 1991Date of Patent: May 25, 1993Assignee: Japan Tobacco Inc.Inventors: Jun-ichi Haruta, Masahiro Tanaka, Itsuo Uchida, Akira Ohta, Shin Hara
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Patent number: 5212324Abstract: A compound for treatment of a cataract which is a 15-ketoprostaglandin compound.Type: GrantFiled: April 3, 1991Date of Patent: May 18, 1993Assignee: R.-Tech Ueno Ltd.Inventor: Ryuji Ueno
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Patent number: 5210277Abstract: This disclosure describes novel compounds, [(1,2,3,4,5-pentaalkyl-2,4-cyclopentadien-1-yl)methyl]glycines, the preparation of the new compounds and their use as intermediates for the preparation of N-phosphonomethylglycine.Type: GrantFiled: March 12, 1992Date of Patent: May 11, 1993Assignee: American Cyanamid CompanyInventor: David A. Cortes
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Patent number: 5204371Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.-or .beta.-position,A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2,--, trans--CH.dbd.CH--, or --CH.tbd.C--, W is hydroxymethylene orD and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.1-10 hydrocarbon aliphatic group substituted by aryl, a substituted aryl as defined for R.sub.2 above, or halogen; or cycloalkyl, substituted cycloalkyl, aryl, substituted aryl or aromatic heterocyclic, all as defined for R.sub.2 above;or a physiologically acceptable salt thereof with a base when R.sub.1 is OH,have valuable pharmacologoical properties.Type: GrantFiled: November 15, 1991Date of Patent: April 20, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 5185374Abstract: A method of inducing uterine contraction which comprises administering, to a subject in need of such contraction, a uterine-contractionally effective amount of a prostanoic acid derivative selected from the group consisting ofa) 15-ketoprostaglandin E compounds, andb) 15-ketoprostaglandin F compounds with the proviso that when the only one group, which is unsubstituted n-pentyl group, is attached to the carbon atom at the 15-position of the prostanoic acid nucleus and the bond between the carbon atoms at 5- and 6-positions is a double bond, then the bond between the carbon atoms at 13- and 14-positions is a single bond.Type: GrantFiled: April 22, 1991Date of Patent: February 9, 1993Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
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Patent number: 5177251Abstract: The present invention relates to a novel class of halogenated tetraenyl prostaglandin compounds represented by the following general formula ##STR1##or a pharmaceutically acceptable salt thereof, whereinY is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --;R.sub.1 is H or a lower alkyl of 1 to 6 carbons;n is an integer from 0 to 3;m is an integer from 0 to 3 and n+m=3; X is Cl or F provided that when X is Cl, n is 2 and m is 1;R.sub.2 and R.sub.3 are independently H, lower alkyl from 1 to 6 carbons, Cl, --CH.sub.2 Cl, --CH.sub.2 F, --CHCl.sub.2, --CCl.sub.3, or taken together form a cycloalkyl of 3 to 6 carbons;R.sub.4 is H, lower alkyl from 1 to 6 carbons, Cl, F or taken together with R.sub.3 form a cycloalkenyl of 4 to 6 carbons; and provided that at least one of --CH.sub.n X.sub.m, R.sub.2, R.sub.3 and R.sub.4 includes a chlorine or fluorine atom.Type: GrantFiled: December 24, 1991Date of Patent: January 5, 1993Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Steven W. Kramer, Robert L. Shone
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Patent number: 5164412Abstract: A Derivative of 5-hetero-6-oxo-PGE A derivative of 5-hetero-6-oxo-PGE of the formula: ##STR1## wherein R.sup.1 is (1) a group of the formula: COOR11(2) hydroxymethylcarbonyl,(3) hydroxymethyl or(4) a group of the formula:CO--AAwherein AA is an amino acid-residue,Z is oxygen, sulfur or a group of the formula: NR21 wherein R21 is hydrogen or alkyl of C1--4;R2 is a single-bond or alkylene of C1--4;R3 isi) alkyl of C1-7,ii) cycloalkyl of C4-7 or cycloalkyl of C4-7 substituted by alkyl of C1-7,iii) phenyl, phenoxy, phenyl or phenoxy substituted by one group selected from alkyl of C1-4, halogen and trihalomethyl, is single-bond or a double bond.Possess PG-like activity, especially cytoprotection, and therefore are useful for treatment for and/or prevention of cytodamage.Type: GrantFiled: April 8, 1991Date of Patent: November 17, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Yoshitaka Konishi, Masanori Kawamura
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Patent number: 5159102Abstract: 7-thiaprostaglandins E.sub.1 which are compounds represented by the following formula [I] or their enantiomers or mixtures thereof in any ratio: ##STR1## where R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.2 -C.sub.20 alkenyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted C.sub.3 -C.sub.10 cycloalkyl group, a substituted or unsubstituted phenyl (C.sub.1 -C.sub.2) alkyl group, or one equivalent cation; R.sup.2 and R.sup.3, which may be the same or different, represent a hydrogen atom, a tri (C.sub.1 -C.sub.7) hydrocarbon silyl group, or a group forming an acetal linkage together with an oxygen atom of a hydroxyl group; R.sup.4 represents a hydrogen atom, a methyl group or a vinyl group; R.sup.5 represents a linear or branched C.sub.3 -C.sub.8 alkyl group, a linear or branched C.sub.3 -C.sub.8 alkenyl group, a linear or branched C.sub.2 -C.sub.Type: GrantFiled: May 22, 1990Date of Patent: October 27, 1992Assignee: Teijin LimitedInventors: Toshio Tanaka, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi
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Patent number: 5157052Abstract: A method is described for inhibiting IgE production which comprises administering, in an amount effective to inhibit IgE production, a prostaglandin of the formula: ##STR1## or a pharmaceutically acceptable non-toxic salt thereof, in which R is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.8 cycloalkyl, phenyl, or mono, di- or tri-substituted phenyl in which the substituents, are selected from the group consisting of bromo, chloro, fluoro, iodo, C.sub.1 -C.sub.5 alkyl, hydroxy, nitro, acetyl, alkoxy, carboxy, acetoxy, amino, mono- or di- alkyl amino, amido and acetamido; R.sub.1 and R.sub.2 independently are hydrogen or C.sub.1 -C.sub.5 alkyl, n.sub.3, n.sub.4, n.sub.5, n.sub.6, n.sub.7, and n.sub.8 independently are zero or one; when n's are zeros, R.sub.3 and R.sub.4 together, R.sub.4 and R.sub.5 together, R.sub.5 and R.sub.6 together, and R.sub.7 and R.sub.8 together are double bonds; when n's are ones, R.sub.3, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 independently are hydrogen, R.sub.Type: GrantFiled: December 27, 1990Date of Patent: October 20, 1992Assignee: Monsanto CompanyInventors: Alan D. Levine, Paul W. Collins
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Patent number: 5153358Abstract: A novel process for the preparation of .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids is disclosed. These .alpha.-alkylated .alpha.-amino acids and .alpha.-halogenated .alpha.-amino acids are useful as intermediates for the preparation of enzyme inhibitors (for example, renin inhibitors) and other peptides or amino acid derivatives or analogs.Type: GrantFiled: January 30, 1991Date of Patent: October 6, 1992Assignee: Abbott LaboratoriesInventor: Thomas M. Zydowsky
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Patent number: 5137915Abstract: The present invention provides novel prostaglandins D, that is, 13,14-dihydro-15-keto-PGDs, which have an excellent sedative and sleep-inducing activity, and so they are useful for tranquilizer and/or soporifics.Type: GrantFiled: June 13, 1991Date of Patent: August 11, 1992Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5117042Abstract: A method of treatment for improving encephalic function which comprises administering, to a subject in need of such treatment, a 15-keto-prostaglandin compound in an amount effective for improvement of encephalic function.Type: GrantFiled: November 21, 1990Date of Patent: May 26, 1992Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuji Ueno, Hiroyoshi Osama, Tomio Oda
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Patent number: 5116869Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.Type: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5113014Abstract: A process for the preparation of a prostaglandin of the formula ##STR1## wherein n is 1, 2, 3 or 4, R.sub.1 and R.sub.2, independently of each other, are alkyl, OH, alkoxy, ketone, halogen, hydrogen, nitro, amino or ether,R.sub.3 is hydrogen, alkyl, haloalkyl or carboxyalkyl,R.sub.4 is hydrogen, alkyl or haloalkyl,R.sub.5 is hydrogen, alkyl or haloalkyl comprising (a) reacting an S-enone of the formula ##STR2## in the presence of a Lewis acid, wherein n is 1, 2, 3 or 4, R.sub.6, R.sub.7 and R.sub.8 are alkyl or any two or three combined are cycloalkyl or aryl,R.sub.9, R.sub.10 and R.sub.11 are alkyl or any two or three combined are cycloalkyl or aryl,R.sub.12 is hydrogen or alkyl(b) reacting the compound from (a) with an aldehyde in the presence of TiCl.sub.4,(c) acetylating the compound from (b),(d) reacting the compound from (c) with Pd(MeCN).sub.2 Cl.sub.Type: GrantFiled: December 13, 1989Date of Patent: May 12, 1992Assignee: Yale UniversityInventors: Samuel J. Danishefsky, Ken H. Chow, Carmen M. P. C. Naves
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Patent number: 5106869Abstract: The present invention provides new compounds, 13,14-dihydro-15-keto-PGFs, and vassopressors containing them, which raise blood pressure without substantial ephemeral depression of blood pressure, trachea or enteron contraction effect inherent in usual PGFs.Type: GrantFiled: September 7, 1990Date of Patent: April 21, 1992Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
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Patent number: 5091113Abstract: R is a straight or branched chain C.sub.4 -C.sub.30 alkyl group, a straight or branched chain C.sub.4 -C.sub.30 alkyl group interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C.sub.5 -C.sub.12 cycloalkyl group, a C.sub.6 -C.sub.10 aryl group, C.sub.6 -C.sub.10 aryl group substituted by one, two or three C.sub.1 -C.sub.12 alkyl groups, a C.sub.7 -C.sub.13 aralkyl group or a C.sub.7 -C.sub.13 aralkyl group which is substituted by a hydroxyl group;R.sub.1 is H or a straight- or branched chain C.sub.1 -C.sub.4 alkyl group;R.sub.2 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group or CO.sub.2 H;R.sub.3 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group, --CH.sub.2 CO.sub.2 H or --CH.sub.2 CH.sub.2 CO.sub.2 H;R.sub.4 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl or CO.sub.2 H;R.sub.5 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group, CH.sub.2 CO.sub.2 H or CH.sub.2 CH.sub.2 CO.sub.Type: GrantFiled: July 27, 1990Date of Patent: February 25, 1992Assignee: Ciba-Geigy CorporationInventor: Brian G. Clubley
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Patent number: 5089524Abstract: Tetraenyl Prostanoic Acid derivatives which are useful as prodrugs for the treatment of peptic ulcer disease and are represented by the following general formula ##STR1## are disclosed.Type: GrantFiled: June 28, 1990Date of Patent: February 18, 1992Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki
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Patent number: 5079259Abstract: A 9-chloroprostane of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha. or .beta.-position and R.sub.1, R.sub.4, R.sub.5, A, B, W, D and E are as described hereinafter which are useful as medical agents.Type: GrantFiled: September 8, 1987Date of Patent: January 7, 1992Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 5077309Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.Type: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5075478Abstract: A process for preparing prostaglandin derivatives by reacting a trans bis-tin ethylene with an organo metal compound then with a compound selected from an epoxide, aldehyde, or ketone, then, without isolation and in the same reaction vessel, reacting with an organo lithium compound, a cuprate complex and a cyclopentenone to produce a prostaglandin intermediate having an unprotected hydroxyl group on the omega side chain.Type: GrantFiled: January 17, 1991Date of Patent: December 24, 1991Assignee: G. D. Searle & Co.Inventors: James R. Behling, John R. Medich
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Patent number: 5073569Abstract: The present invention provides novel prostaglandins D, that is, 13,14-dihydro-15-keto-PGDs, which have an excellent sedative and sleep-inducing activity, and so they are useful for tranquilizer and/or soporifics.Type: GrantFiled: September 6, 1989Date of Patent: December 17, 1991Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5055592Abstract: This invention relates to the novel processes for the preparation of a 16-methoxy-16-methyl prostaglandin E.sub.1 derivative and to the novel intermediates useful therefor.Type: GrantFiled: January 30, 1990Date of Patent: October 8, 1991Assignee: Merrell Dow PharmaceuticalsInventors: Michael Kolb, Luc Van Hijfte
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Patent number: 5055604Abstract: A process for preparing a prostaglandin derivative by reacting an alkyne with zirconocene chloride hydride to produce a zirconium intermediate which is reacted with an alkyllithium and a first copper reagent selected from R.sup.2 Cu(CN)Li or the mixture CuCN and R.sup.2 Li to produce a higher order cuprate complex intermediate and reacting the higher order cuprate complex intermediate with a cyclopentenone to produce the prostaglandin derivative.Type: GrantFiled: April 17, 1990Date of Patent: October 8, 1991Assignee: G. D. Searle & Co.Inventors: Kevin A. Babiak, James R. Behling, John H. Dygos, John S. Ng
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Patent number: 5025034Abstract: Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.Type: GrantFiled: February 7, 1990Date of Patent: June 18, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5023273Abstract: The invention relates to 6-oxo-prostaglandin E.sub.1 derivatives of formula I, ##STR1## in which R.sup.1 means the radical COOR.sup.2 with R.sup.2 meaning a hydrogen atom, C.sub.1 -C.sub.10 alkyl, a C.sub.5 -C.sub.6 cycloalkyl or a C.sub.6 -C.sub.10 aryl group or a heterocyclic radical, or the radical CONHSO.sub.2 R.sup.5 as C.sub.1-10 alkyl, C.sub.5-6 cycloalkyl or C.sub.6-10 aryl,A means an E-configuration CH.dbd.CH or a --C.dbd.C group,W means a free or functionally modified hydroxymethylene group or a free or functionally modified group, and the OH group in each case can be in the alpha or beta position,D means a straight-chain or branched-chain alkylene group with 1-5 C atoms,E means a --C.dbd.C group or a C.sub.2 -C.sub.4 alkenylene group,R.sup.3 means C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl or an optionally substituted C.sub.6 -C.sub.10 aryl group or a heterocyclic group,R.sup.4 means a free or functionally modified hydroxy group, and if R.sup.Type: GrantFiled: November 23, 1988Date of Patent: June 11, 1991Assignee: Schering AktiengesellschaftInventors: Ulrich Klar, Werner Skuballa, Helmut Vorbruggen, Claus-Steffen Sturzebecher, Karl-Heinz Thierauch, Ekkehard Schillinger
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Patent number: 5001153Abstract: The present invention relates to ocular hypotensive agents which contains 13,14-dihydro-15-keto-prostagrandins, which shows no transient ocular hypertensive response that PGs usually show.Type: GrantFiled: September 19, 1988Date of Patent: March 19, 1991Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
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Patent number: 4990662Abstract: Catalyst and process are disclosed for the improved preparation of alpha, beta-unsaturated acids. The catalyst comprises a porous silica gel component and a Group IA alkali metal component, which is present in an amount of from 200 to 20,000 parts per million and optionally another component such as tin (IV) oxide, and mixtures thereof. The process comprises reacting formaldehyde and an aliphatic carboxylic acid in the presence of said catalyst while maintaining catalyst activity and selectivity during the process by addition of a source of the alkali metal component.Type: GrantFiled: July 27, 1987Date of Patent: February 5, 1991Assignee: Amoco CorporationInventors: Gary P. Hagen, Ruth A. Montag
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Patent number: 4983629Abstract: 11-Haloprostane derivatives of general Formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or a --C.tbd.C--group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: June 21, 1989Date of Patent: January 8, 1991Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4983753Abstract: Novel compounds are disclosed of the classes: ##STR1## wherein the subscript n is an integer from 3-5, inclusive, R.sub.1 is hydrogen or R.sub.2 ; R.sub.2 and R.sub.3 consist essentially of C.sub.1 -C.sub.6 alkyl and R.sub.2 may be the same as or different from R.sub.3, and wherein Aryl consists essentially of phenyl and phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, and trifluoromethyl;(b) derivatives of furan having the formula ##STR2## wherein R.sub.4 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, and W is either carbonyl or carbinol; and(c) cyclopentenonyl compounds having the formulas ##STR3## wherein R.sub.5 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, P.sub.Type: GrantFiled: June 23, 1989Date of Patent: January 8, 1991Inventor: Middleton B. Floyd, Jr.
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Patent number: 4981872Abstract: Prostaglandin derivatives having an oxo group at specified positions in the .alpha. side chain have a variety of physiological effects, notably a strong anti-ulcer activity accompanied by a limited ability to inhibit blood platelet aggregation.Type: GrantFiled: January 15, 1988Date of Patent: January 1, 1991Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Keiichi Tabata, Nobuyoshi Iwata
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Patent number: 4943659Abstract: Catalyst and process are disclosed for preparation of alpha, beta-unsaturated acids. Catalyst comprises a silica component and a Group IA alkali metal component which is present in an amount of from 200 to 15,000 parts per million, said silica component containing less than about 500 parts per million individually of aluminum, zirconium, titanium, iron and mixtures thereof. Process comprises reacting formaldehyde and a carboxylic acid of the formula RHC.sub.2 COOH wherein R is a member of the class consisting of --H, -alkyl, -aryl, -aralkyl, -cycloalkyl, and -alkylaryl radicals in the presence of said catalyst. Catalyst activity is maintained during process by addition of source of alkali metal component.Type: GrantFiled: December 29, 1986Date of Patent: July 24, 1990Assignee: Amoco CorporationInventor: Gary P. Hagen
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Patent number: 4942256Abstract: This invention relates to several novel intermediates useful in the manufacture of thromboxane A.sub.2 inhibiting 7-[3-.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2. 1]-heptenoic acids.Type: GrantFiled: December 13, 1988Date of Patent: July 17, 1990Assignee: National Research Development CorporationInventors: Robert B. Garland, Masateru Miyano
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Patent number: 4927964Abstract: An advantageous method of producing in large amounts on a commercial scale 2-substituted oxyimino-3-oxobutyric acids, which are useful as intermediates in the synthesis of e.g. aminothiazole cephalosporins, is characterized by reacting a tert-butyl 2-substituted oxyimino-3-oxobutyrate with a hydrogen halide in an anhydrous organic solvent.Type: GrantFiled: January 11, 1989Date of Patent: May 22, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Yukio Ishibashi, Haruo Shinbo
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Patent number: 4921995Abstract: A novel process for manufacturing 16-substituted .DELTA..sup.7 -prostaglandin Es, which include compounds expressed by the following formula (I), their enanantiomers, or their mixtures of arbitrary mixing ratio, ##STR1## wherein R.sup.1 indicates COOR.sup.2, CH.sub.2 OR.sup.3, or COCH.sub.2 OR.sup.3, in which R.sup.2 indicates a hydrogen atom, a substituted or unsubstituted C.sub.1 -C.sub.10 alkyl group, a substituted or unsubstituted C.sub.3 -C.sub.10 cycloalkyl group, or a substituted or unsubstituted phenyl group, and R.sup.3 indicates a hydrogen atom, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group, a group which forms an acetal bond together with the oxygen atom of a hydroxyl group, or a C.sub.2 -C.sub.7 acyl group; R.sup.4 and R.sup.5 are identical or different, each representing a hydrogen atom, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group, or a group which forms an acetal bond together with the oxygen atom of a hydroxyl group; R.sup.6 indicates a hydrogen atom, a C.sub.1 -C.sub.Type: GrantFiled: February 9, 1988Date of Patent: May 1, 1990Assignee: Teijin LimitedInventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi, Masahiro Koga
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Patent number: 4908475Abstract: New compounds which have potent V.sub.2 -vasopressin antagonistic activity are prepared by a 1,6-cyclization using peptide bond formation. The structures of the compounds are characterized by a Pas.sup.1,6 or Tas.sup.1,6 cyclized unit. Also a chiral synthesis of the optically pure Pas intermediates is described.Type: GrantFiled: May 9, 1988Date of Patent: March 13, 1990Assignee: SmithKline Beckman CorporationInventors: James F. Callahan, William F. Huffman, Kenneth A. Newlander, Nelson C. F. Yim
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Patent number: 4906663Abstract: A 6-fluoroprostaglandin having the formula: ##STR1## wherein A is a carbonyl group or a hydroxymethylene group, R.sup.1 is a substituted or unsubstituted C.sub.1 -C.sub.10 alkyl group or a substituted or unsubstituted 5- or 6-membered cycloalkyl group, R.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, each of R.sup.3 and R.sup.4 which may be the same or different is a hydrogen atom or a protecting group, R.sup.5 is a hydrogen atom or a hydroxyl group, and is a single bond or a double bond, and its salt when R.sup.2 is a hydrogen atom.Type: GrantFiled: October 14, 1988Date of Patent: March 6, 1990Assignees: Asahi Glass Company, Ltd., Dainippon Pharmaceutical Company, Ltd.Inventors: Naonobu Hatano, Buichi Fujitani, Toshiaki Kadokawa, Yasushi Matsumura, Tomoyuki Asai, Arata Yasuda, Keiichi Uchida
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Patent number: 4904820Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as 1,4-conjugate addition. The complex is formed by reacting a first cuprate cmoplex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes prepared by this process are particularly useful for the efficient preparation of pharmacologically active prostaglandins.Type: GrantFiled: July 14, 1988Date of Patent: February 27, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, James R. Behling
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4898930Abstract: Peptide ester and amide derivatives of the general formula I: ##STR1## in which X is H or an acyl, A and B are structurally defined amino acid residues, n is an integer of from 1 to 3, R.sup.1 is H or a lower alkyl and either R.sup.2 or C is a defined optionally modified amino acid residue and the other is a lower alkoxyl, an amino group or a direct chemical bond, are converted under physiologic conditions, by enzymic hydrolysis in pathologically altered tissues and subsequent spontaneous cyclization, into pharmacodynamically active spirocyclic peptide derivatives of the general formula III: ##STR2## in which R.sup.3 and R.sup.4 are H atoms, optionally substituted alkyl groups or jointly an aliphatic chain forming preferably a 2,5- piperazinedione ring, and hence can act as pro-farmaca (drug precursors) of prolonged biological effect.Type: GrantFiled: June 12, 1987Date of Patent: February 6, 1990Assignee: Spofa, spojene podniky proInventors: Evzen Kasafirek, Miroslav Rybak, Ivan Krejci, Antonin Sturc, Alena Roubalova, Jiri Vanzura, Evzen Krepela, Michal Bartik
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Patent number: 4894473Abstract: A multistep process for preparing 7-(2-hexyl-5-hydroxy-cyclopentyl)-heptanoic acid is described. Novel intermediates are also described.Type: GrantFiled: November 5, 1987Date of Patent: January 16, 1990Assignee: Istituto Biochimico Italiano Giovanni Lorenzini S.p.A.Inventors: Umberto Valcavi, Sergio Innocenti, Enrico Bosone, Paolo Farina, Vittorio Marotta, Gianbattista Zabban
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Patent number: 4888358Abstract: Novel 13,14-dihydroprostaglandin derivatives of the formula ##STR1## wherein: m is 1 or 3;R.sub.1 is hydrogen or alkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 and R.sub.4 are independently hydrogen or methyl;R.sub.5 is alkyl, CF.sub.3 (CH.sub.2).sub.n -- in which n is an integer of 3-5, cycloalkyl, or optionally substituted phenyl, benzyl or phenoxy; orR.sub.4 and R.sub.5 taken together with the carbon to which they are attached is cycloalkyl of 4-8 carbon atoms;X is cis --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 -- when m is 3, orX is --CH.sub.2 CH.dbd.C.dbd.CH-- when m is 1;and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.;or a pharmaceutically acceptable salt thereof,have been prepared. They are useful in particular for their antihypertensive and anti-ulcerogenic properties.Type: GrantFiled: August 25, 1988Date of Patent: December 19, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Joan Huguet, Joseph M. Muchowski, Maria T. Lara
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Patent number: 4886903Abstract: The present invention provides a process for the production of PGD.sub.2, wherein 7-hydroxy prostaglandin F.sub.2 .alpha. is treated with thiocarbonyl diimidazole or its analog and subjecting thus treated product to the reaction to deoxidize the hydroxyl group at the 7-position, the reaction to convert the hydroxyl group to a protecting group, and the reaction to oxidize the hydroxyl group at the 11-position, thus giving PGD.sub.2 at a high efficiency.Type: GrantFiled: September 13, 1988Date of Patent: December 12, 1989Assignee: Teijin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Akira Yanagisawa, Seizi Kurozumi
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Patent number: 4879403Abstract: Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.Type: GrantFiled: November 2, 1988Date of Patent: November 7, 1989Assignee: Hoechst AktiengesellschaftInventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
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Patent number: 4874803Abstract: The present invention comprises reaction products resulting from the reaction of hydrazido-substituted or certain amino-substituted polymer stabilizers and cyclic dianhydrides, as well as the use of such products. The polymer stabilizers of the invention are useful for protecting a large variety of synthetic polymeric organic materials from the degradative effects of heat, light and oxygen. Some of the modifiers are flame retardants and many are metal deactivators in addition to their primary activity.Type: GrantFiled: September 21, 1987Date of Patent: October 17, 1989Assignee: Pennwalt CorporationInventors: Arthur L. Baron, Terry N. Myers, Jerome Wicher
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Patent number: 4873360Abstract: Cyclopentanoids (I) of the formula: ##STR1## including stereoisomers are described along with a process for the preparation of I. In particular the preparation of prostanoids of the formula: ##STR2## wherein R.sub.1 is a alkyl group containing 1 to 8 carbon atoms and R.sub.2 CO.sub.2 R.sub.3 is an alkenyl ester group, R.sub.2 contains 2 to 6 carbon atoms and R.sub.3 is a lower alkyl group containing 1 to 6 carbon atoms is described. A particular prostaglandin prepared by the process is PGE.sub.2. The prostanoids have been demonstrated to have pharmacological activity in animals and humans. Novel intermediates of (I) are also described.Type: GrantFiled: January 21, 1988Date of Patent: October 10, 1989Assignee: Board of Governors of Wayne State UniversityInventors: Carl R. Johnson, Thomas D. Penning
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Patent number: 4870104Abstract: 11-Haloprostane derivatives of general formula I ##STR1## wherein X is F, Cl or Br,R.sub.1 is the residue CH.sub.2 OH or ##STR2## wherein R.sub.2 means a hydrogen atom, an alkyl, cycloalkyl, aryl, phenacyl or heterocyclic residue,A is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH-group,B is a --CH.sub.2 --CH.sub.2 -- or trans-CH.dbd.CH-- or a --C.tbd.C-group,W is an ethylenedioxymethylene group or a hydroxymethylene group,D and E together mean a direct bond orD is a C.sub.1-10 -alkylene group,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C-bond or a --CR.sub.6 .dbd.CR.sub.7 -group with R.sub.6 and R.sub.7 meaning a hydrogen atom, a chlorine atom or an alkyl group,R.sub.4 is a hydroxy group,R.sub.5 is a hydrogen atom, an alkyl, a cycloalkyl, an aryl or a heterocyclic group, andthe salts thereof with physiologically compatible bases, processes for their preparation, and use thereof as agents inhibiting gastric acid secretion.Type: GrantFiled: November 12, 1986Date of Patent: September 26, 1989Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Claus-Steffen Sturzebecher, Walter Elger
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Patent number: 4849535Abstract: Cyclopentenylheptanoic acid derivatives having the formula: ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.4 alkyl and --(A)-- is: ##STR2## wherein M is hydrogen or triorganosilyl group, are prepared by reacting a compound having the formula: ##STR3## ps wherein X is halogen, with a compound having the formula: The derivatives belong to the pharmacologically-active class of compounds called "prostaglandins".Type: GrantFiled: February 24, 1986Date of Patent: July 18, 1989Assignees: Ajinomoto Co., Inc., Mochida Pharmaceutical Co., Ltd.Inventors: Hirokazu Naora, Takashi Onuki, Asao Nakamura