Cyclopentyl In Acid Moiety (e.g., Prostaglandins, Etc.) Patents (Class 560/121)
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Patent number: 6066751Abstract: It has been surprisingly discovered that the disadvantages of the lengthy literature procedures to synthesize 13,14-dihydro prostaglandin A, E, and F derivatives can be overcome using a novel Methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2 tetramethyl-1-silapropoxy)cyclopentyl) heptanoate intermediate, which can be synthesized from commercially available Methyl 7-[3-(R)-hydroxy-5-oxo-1-cyclopent-1-yl] heptanoate. This novel intermediate can be coupled with oxygen, carbon, sulfur, and nitrogen nucleophiles, in the presence of a base or a Lewis acid, in a ring-opening process to provide 13,14-dihydro prostaglandin A, E, and F derivatives.Type: GrantFiled: September 4, 1998Date of Patent: May 23, 2000Assignee: The Procter & Gamble CompanyInventors: John August Wos, Jack Snyder Amburgey, Jr., Mitchell Anthony deLong, Yili Wang, Haiyan George Dai, Biswanath De
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Patent number: 6043275Abstract: A 3,7-dithiaprostanoic acid derivative of the formula (I) ##STR1## (wherein, R.sup.1 is OH, C1.about.6 alkyloxy, NR.sup.6 R.sup.7 (R.sup.6, R.sup.7 are H, C1.about.6 alkyl.); R.sup.2 is H, OH; R.sup.3 is single bond, C1.about.6 alkylene; R.sup.4 is (i) C1.about.8 alkyl substituted by C1.about.6 alkyloxy, halogen etc., (ii) phenyloxy, C3.about.7 cycloalkyloxy, (iii) furyl, furyloxy, thienyl, thienyloxy, naphthyl, naphthyloxy, phthalanyl, phthalanyloxy, (iv) phenyl, phenyloxy, C3.about.7 cycloalkyl, C3.about.7 cycloalkyloxy substituted by C1.about.6 alkyl etc., (v) furyl, furyloxy, thienyl, thienyloxy, naphthyl, naphthyloxy, phthalanyl, phthalanyloxy substituted by C1.about.6 alkyl etc.; R.sup.5 is H, C1.about.6 alkyl.) can bind PGE.sub.2 receptor (particularly, EP4 subtype receptor) strongly. So, they are useful for the prevention and/or treatment of immunological diseases (autoimmune diseases, rejection after organ transplantation etc.Type: GrantFiled: April 8, 1999Date of Patent: March 28, 2000Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Toru Maruyama, Shuichi Ohuchida
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Patent number: 6025518Abstract: A substituted cyclopentene derivative of formula (V): whereinX.sup.1 is (.alpha.-OZ.sup.a, .beta.-H) or (.alpha.-H, .beta.-OZ.sup.a), X.sup.3 is (.alpha.-OZ.sup.d, .beta.-H), (.alpha.-H, .beta.-OZ.sup.d), or oxygen atom, each of Z.sup.a and Z.sup.d, which may be the same or different, is a hydrogen atom or a protective radical for a hydroxyl radical;U is a radical selected from the group consisting of CR.sup.1 HCH.sub.2, CR.sup.1 .dbd.CH and C.tbd.C,whereinR.sup.1 is a hydrogen atom, halogen atom, substituted silyl radical represented by SiR.sup.9 R.sup.10 R.sup.11 or substituted stannyl radical represented by SnR.sup.14 R.sup.15 R .sup.16,m is an integer of 0 to 6;X.sup.2 is CH.dbd.CH or C.tbd.C,p is an integer of 0 or 1, each of n and q is an integer of 0 to 5; andZ.sup.1 is a hydrogen atom, COOR.sup.y, CN, OH, OCOR.sup.2, CONR.sup.b R.sup.c or NR.sup.d R.sup.e.Type: GrantFiled: September 8, 1998Date of Patent: February 15, 2000Assignees: Nissan Chemical Industries, Ltd., Fumie SATOInventor: Fumie Sato
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Cyclopentane (ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents
Patent number: 5990138Abstract: The invention relates to 7-[5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxycyclopentyl(enyl)] heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.Type: GrantFiled: January 4, 1999Date of Patent: November 23, 1999Assignee: AllerganInventor: Robert M. Burk -
Patent number: 5990346Abstract: A prostaglandin having formula (I), (II), or (III): ##STR1## a process of production thereof, and inhibitors of cell migration caused by chemokines containing (I) or (II) as an active ingredient.Type: GrantFiled: February 26, 1997Date of Patent: November 23, 1999Assignee: Teijin LimitedInventors: Kenichiro Kataoka, Toru Minoshima, Tatsuki Shiota, Takaharu Tsutsumi, Takahiko Hada, Hiroko Tanaka, Takuya Morita, Noriaki Endo
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Patent number: 5986095Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.Type: GrantFiled: January 6, 1992Date of Patent: November 16, 1999Assignee: E.R. Squibb & Sons, Inc.Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5985920Abstract: A fluorine-containing prostaglandin derivative of the formula (1) (or a salt thereof) and a medicine containing it, particularly, a preventive or therapeutic medicine for an eye disease: ##STR1## wherein A is a vinylene group or the like, R.sup.1 is an aryloxyalkyl group or the like, R.sup.2 and R.sup.3 are hydrogen atoms or the like, and Z is OR.sup.4 (wherein OR.sup.4 is a hydrogen atom or an alkyl group) or the like.Type: GrantFiled: August 3, 1998Date of Patent: November 16, 1999Assignees: Asahi Glass Company Ltd., Santen Pharmaceutical Co., Ltd.Inventors: Eiichi Shirasawa, Masaaki Kageyama, Tadashi Nakajima, Takashi Nakano, Nobuaki Mori, Hideshi Sasakura, Yasushi Matsumura, Yoshitomi Morizawa
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Patent number: 5962724Abstract: The present invention relates to a highly enantioselective process for the preparation of enantiomerically pure cyclopentane- and -pentene .beta.-amino acids of the general formula (I) ##STR1## in which A and L, A and D or E and L, D and E, R.sup.2, R.sup.3, T and R.sup.1 have the meaning given in the description.Type: GrantFiled: July 5, 1996Date of Patent: October 5, 1999Assignee: Bayer AktiengesellschaftInventors: Joachim Mittendorf, Hermann Arold, Peter Fey, Michael Matzke, Hans-Christian Militzer, Klaus-Helmut Mohrs
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Patent number: 5935939Abstract: The present invention provides for stabilization of misoprostol in solid dispersions using amorphous excipients or excipients which have been converted to an amorphous state such as hydroxypropyl cellulose, methyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, cellulose acetate phthalate, cellulose acetate butyrate, hydroxyethyl cellulose, ethyl cellulose, polyvinyl alcohol, polyethylene glycol, starch, polypropylene, dextrans, dextrins, hydroxypropyl .beta.-cyclodextrin chitosan, co-(lactic/glycolic)copolymers, poly(orthoester), polyvinyl chloride, polyvinyl acetate, ethylene vinyl acetate, lectins, carbopols, silicon elastomers, cyclodextrins, polyacrylic polymers, maltodextrins, lactose, fructose, inositol, trehalose, maltose, and raffinose, (and other mono-, di- and tri- saccharides) and .alpha.-, .beta.- and .gamma.-cyclodextrins, and more preferably the excipients which are used are dextran, maltodextrin, hydroxypropyl .beta.-cyclodextrin and maltose.Type: GrantFiled: September 9, 1996Date of Patent: August 10, 1999Assignee: G. D. Searle & Co.Inventors: Tugrul T. Kararli, David Otto, Stanley C. Penzotti, Jr., James E. Truelove
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Patent number: 5891910Abstract: The invention relates to 9-halogen-(Z) prostane derivatives of formula I ##STR1## in which ##STR2## Z represents the radicals Hal represents a chlorine or fluorine atom,R.sub.1 represents ##STR3## A represents a --CH.sub.2 --CH.sub.2 --, a trans--CH=CH or --C.ident.C, W represents a free or a functionally modified ##STR4## group, D and E together represent a direct bond orD represents a straight-chain alkylene group with 1-10 C atoms, a branched-chain alkylene group with 2-10 C atoms or an annular alkylene group with 3-10 C atoms, which optionally can be substituted by fluorine atoms, andE represents an oxygen or sulfur atom, a direct bond, a C.ident.C bond or a --CR.sub.6 =CR.sub.7 group, and R.sub.6 and R.sub.7 are different and mean a hydrogen atom, a chlorine atom or a C.sub.1 -C.sub.4 alkyl group,R.sub.4 represents a free or functionally modified hydroxy,R.sub.5 means a hydrogen atom, an alkyl, a halogen-substituted alkyl, a cycloalkyl or an optionally substituted aryl or a heterocyclic group.Type: GrantFiled: June 6, 1995Date of Patent: April 6, 1999Assignee: Schering AktiengesellschaftInventors: Bernd Buchmann, Werner Skuballa, Helmut Vorbrueggen, Bernd Raduechel, Olaf Loge, Walter Elger, Claus-Steffen Stuerzebecher, Karl-Heinz Thierauch
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Patent number: 5892099Abstract: A 3,7-dithiaprostanoic acid derivative of the formula (I) ##STR1## (wherein R.sup.1 is OH, C1-4 alkoxy, NR.sup.6 R.sup.7 (wherein R.sup.6, R.sup.7 are H, C1-4);R.sup.2 is H, OH; R.sup.3 is (i)alkyl, alkenyl, alkynyl (ii) phenyl, cycloalkyl (iii) alkyl, alkenyl, alkynyl substituted by phenyl, cycloalkyl (when R.sup.2 is H, alkyl, alkenyl, alkynyl in (i) or (iii) may be substituted by OH) possesses a binding activity for PGE.sub.2 receptor (especially for EP4). Therefore they are useful for the treatment and/or prevention of immunologic diseases (autoimmune diseases, immunological deficiency diseases, organ transplantation etc.), asthma, abnormal bone formation, neuronal cell death, liver damage, nephritis, hypertension, myocardiac ischemia etc.Type: GrantFiled: January 27, 1998Date of Patent: April 6, 1999Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Toru Maruyama, Shuichi Ohuchida
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Patent number: 5886034Abstract: 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: March 10, 1995Date of Patent: March 23, 1999Assignee: Kabushiki Kaisha Ueno Seiyaku KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5874600Abstract: A catalyst of ruthenium (II) which includes bidentate phosphine ligands. The catalyst is obtainable by a process which includes the steps of treating equimolar amounts of an appropriate Ru(II) complex and a bidentate diphosphine ligand with an acid of formula HX, wherein X is a non-coordinating anion. The acid is used in a ratio which does not exceed 2 molar equivalents per mole of Ru(II) complex and the treatment is carried out in a non-coordinating or weakly coordinating solvent and under an inert atmosphere. This catalyst is useful for the preparation of the preferred isomer of HEDIONE, having the (+)-(1R)-cis-configuration.Type: GrantFiled: July 10, 1997Date of Patent: February 23, 1999Assignee: Firmenich SAInventors: Valentin Rautenstrauch, Koenraad P. M. Vanhessche, Jean-Pierre Genet, Jean-Yves Lenoir
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Patent number: 5859283Abstract: 4-Substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meanings defined in the description, which possess valuable herbicidal properties and intermediates useful in their preparation.Type: GrantFiled: February 11, 1998Date of Patent: January 12, 1999Assignee: Rhone-Poulenc Agriculture LimitedInventor: Susan Mary Cramp
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Patent number: 5827883Abstract: A method of using vitamin D derivatives of the formula ##STR1## wherein X is .dbd.CH.sub.2 or H,H;Y is a moiety--CH(CH.sub.3)--(A).sub.n --C(O)--OR.sup.1 (a)--CH(CH.sub.3)--CH.sub.2 --O--C(O)--R.sup.2 (b)or--C(O)--OR.sup.1 (c);A is --CH.dbd.CH-- or CH.sub.2 --CH.sub.2 --R.sup.1 is lower alkyl, cycloalkyl, cycloalkylmethyl, --CH.sub.2 R.sup.3 or --CH.sub.2 --CH.sub.2 R.sup.3 ;R.sup.2 is lower alkyl, cycloalkyl or R.sup.3 ;R.sup.3 is hydroxy-lower alkyl, hydroxy-cycloalkyl or trifluoromethyl-hydroxy-lower-alkyl;n is 0 or 1;and the dotted bond in the five membered ring is optional;in the treatment of dermatological conditions, in particular keratinization disorders such as psoriasis, as well as acne and photodamaged skin, is described.Vitamin D derivatives of the formula I above, wherein X, Y, A, R.sup.1, R.sup.2, R.sup.3 and n are as set forth above; with the proviso that X is H,H when Y is --CH(CH.sub.3)--CH.sub.2 --OC(O)--C(OH)(CH.sub.3).sub.Type: GrantFiled: July 21, 1997Date of Patent: October 27, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Pierre Barbier, Marc Muller, Josef Stadlwieser
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Patent number: 5817694Abstract: Analogs of the prostaglandin PGE.sub.1 are disclosed. These compounds exhibit uterotonic properties, enhancing the response to PGF.sub.2 .alpha. in isolated rat uteri. The compounds also exhibit other pharmacological properties, as inhibitors of gastric acid secretion, hypotensives, and bronchodilators. Processes for making the analogs, useful intermediates, and pharmaceutical preparations are also presented.Type: GrantFiled: June 4, 1993Date of Patent: October 6, 1998Assignee: New Pharma International Corp.Inventors: Carlos Alberto Genaro Mammarella, Carlos Alberto Buschi, Silvia Susana Giarcovich
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Patent number: 5807892Abstract: Certain prostaglandin analogues are useful in the treatment of glaucoma and ocular hypertension. Also disclosed are ophthalmic, pharmaceutical compositions comprising such prostaglandin analogues.Type: GrantFiled: June 7, 1995Date of Patent: September 15, 1998Assignee: Alcon Laboratories, Inc.Inventors: Peter G. Klimko, Robert D. Selliah, Thomas R. Dean, Mark R. Hellberg, John E. Bishop
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Patent number: 5783602Abstract: The invention relates to leukotriene-B.sub.4 derivatives of general formula I, ##STR1## in which R.sub.1 represents CH.sub.2 OH, CH.sub.3, CF.sub.3 COOR.sub.4 CONR.sub.5 R.sub.6, andR.sub.3 symbolizes H; C.sub.1 -C.sub.14 alkyl, C.sub.3 -C.sub.10 cycloalkyl optionally substituted singly or multiply; C.sub.6 -C.sub.10 aryl radicals, independently of one another, optionally substituted singly or multiply by halogen, phenyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoromethyl, chloromethyl, trifluoromethyl, carbonyl, carboxyl or hydroxy; or a 5- to 6-membered aromatic heterocyclic ring with at least 1 heteroatom,X and Y mean a direct bond, whereby the resulting olefin can be E- or Z-configured or X represents a fluorine atom in .alpha.- or .beta.-position, and Y means a hydrogen atom in .beta.-position.Type: GrantFiled: December 4, 1996Date of Patent: July 21, 1998Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5770759Abstract: 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: August 23, 1996Date of Patent: June 23, 1998Assignee: R-Tech Ueno, Ltd.Inventors: Ryuzo Ueno, Ryuji Ueno, Tomio Oda
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Patent number: 5760277Abstract: The cycloaliphatic ketones of formula ##STR1## having two conjugated double bonds in positions 1 and 3, or 2 and 4, such as indicated by the dotted lines, and wherein R defines a C.sub.1 to C.sub.Type: GrantFiled: January 15, 1997Date of Patent: June 2, 1998Assignee: Firmenich SAInventors: Ferdinand Naef, Rene Decorzant
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Patent number: 5756818Abstract: The invention relates to 9-chloro-prostaglandin derivatives of formula I ##STR1## in which X means oxygen or CH.sub.2,R.sup.1 means hydrogen or straight-chain or branched alkyl with 1-6 C atoms andA means trans-CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,as well as their salts with physiologically compatible bases, if R.sup.1 represents hydrogen, and their clathrates with .alpha.-, .beta.- or .gamma.-cyclodextrin, process for their production and their pharmaceutical use.Type: GrantFiled: May 29, 1996Date of Patent: May 26, 1998Assignee: Schering AktiengesellschaftInventors: Bernd Buchmann, Werner Skuballa
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Patent number: 5739161Abstract: The object of the present invention is to provide a pharmaceutical composition for treatment of hepato.biliary disease reduced in side effect such as diarrhea, which comprises 16,16-difluoro-15-keto-PGs having at least one methyl group or ethyl group on the carbon atom at the 17- or 18-position or adjacent to the terminal methyl group of .omega.-chain as an essential component.Type: GrantFiled: February 12, 1997Date of Patent: April 14, 1998Assignee: R-Tech Ueno, Ltd.Inventor: Ryuji Ueno
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Patent number: 5736274Abstract: A polymer containing a recurring unit of a conjugated N-fluoropyridinium salt and an active material for a positive electrode, an electrolyte, a battery material for the positive electrode and a battery which use such a polymer. That polymer provides a battery material and a primary battery or a secondary battery which have high electromotive force, high energy density, high environmental acceptability, a low internal resistance in charging and discharging and strong recoverability of the electromotive force, and can be useful as a fluorinating agent.Type: GrantFiled: April 18, 1997Date of Patent: April 7, 1998Assignee: Daikin Industries, Ltd.Inventors: Teruo Umemoto, Kenji Adachi, Ginjiro Tomizawa, Sumi Ishihara, Masayuki Nagayoshi
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Patent number: 5731452Abstract: 7-thiaprostaglandins having the formula (I) which inhibit cell migration induced by monocyte chemoattractant protein MCP-1/MCAF and other chemokines and can serve as drugs for the treatment of atherosclerosis, diabetic angiopathy, and other disorders, their enantiomers, mixtures of the same, and methods of production thereof.Type: GrantFiled: September 18, 1995Date of Patent: March 24, 1998Assignee: Teijin LimitedInventors: Toru Minoshima, Kenichiro Kataoka, Hiroko Tanaka, Koji Ishii, Noriaki Endo
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Patent number: 5698590Abstract: Prostaglandin E.sub.1 ester derivatives of the formula (I): ##STR1## wherein the R' groups are the same as each other and are C4-12 alkyl; or cyclodextrin clathrates thereof, liposome formulations containing them, and pharmaceutical compositions containing them, as active ingredient.The compounds of formula (I) have the effect of increasing blood flow and are useful for the prevention and/or treatment of peripheral circulatory disorder, decubitus, or skin ulcers, or for the maintenance of blood flow.Type: GrantFiled: August 22, 1996Date of Patent: December 16, 1997Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Akio Nishiura, Takuya Seko, Ryoji Matsumoto, Shin-ichi Hamano
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Patent number: 5690957Abstract: Prostaglandin E, ester derivatives of the formula (I): ##STR1## wherein R is (i) --CH.sub.2 CH.sub.2 --O--CO--R.sup.1(ii) --CH.sub.2 CH.sub.2 --O--CO--CH.sub.2 --O--R.sup.2, andR.sup.1 and R.sup.2 each independently is C10-20 alkyl;and cyclodextrin clathrates thereof, liposome formulations containing them, and pharmaceutical compositions containing them as active ingredient.The compounds of formula (I) have the effect of increasing blood flow and are useful for the prevention and/or treatment of peripheral circulatory disorder, decubitus, or skin ulcers, or for the maintenance of blood flow.Type: GrantFiled: August 14, 1996Date of Patent: November 25, 1997Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Akio Nishiura, Takuya Seko, Ryoji Matsumoto, Shin-ichi Hamano
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Patent number: 5684177Abstract: In a process for making synthetic prostaglandin-type compounds such as misoprostol, organo metallic cuprate complexes capable of reacting with cyclopentenones are prepared by reaction of an alkyl lithium compound with a cuprous halide, followed by reaction of the resulting complex with a vinyl stannane, using an excess of alkyl lithium in the initial reaction and maintaining the excess present during the formation of the organo metallic cuprate complex.Type: GrantFiled: May 17, 1996Date of Patent: November 4, 1997Assignee: Torcan Chemical Ltd.Inventors: Yee-Fung Lu, Raymond So, Dan To, Casimir G. Antczak
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Patent number: 5663417Abstract: (1) Prostaglandin (PG) E.sub.2 antagonist or agonist containing carbocyclic sulfonamides represented by the compound of the formula (I): ##STR1## cyclodextrin clathrates thereof, non-toxic salts thereof as active ingredient, (2) carbocyclic sulfonamides represented by the compound of the formula (II): ##STR2## cyclodextrin clathrates thereof, non-toxic salts thereof, (3) process for the preparation of the compound represented by the compound of the formula (II) described hereinbefore, (4) PGE.sub.2 antagonist or agonist containing the compound represented by the compound of the formula (II) as active ingredient.The compounds represented by the compounds of the formula (I) and (II) can be adapted to medicines which possess an inhibitory effect of uterine contraction, an analgetic action, an inhibitory effect of digestive peristalsis, a sleep-inducing effect as PGE.sub.Type: GrantFiled: January 27, 1994Date of Patent: September 2, 1997Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Nobuyuki Hamanaka, Tsumoru Miyamoto
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Patent number: 5639899Abstract: Object: To provide novel prostaglandin E.sub.1 analogues which have more excellent pharmaceutical effects, longer duration of the effects and less side-effects than the prior art prostaglandin E.sub.1 's.Constitution: A PGE.sub.1 analogue represented by the formula: ##STR1## (wherein A is a vinylene group or an ethynylene group, R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an allyl group, R.sup.2 is a branched aliphatic hydrocarbon group having 5 to 10 carbon atoms), or a salt thereof.Type: GrantFiled: October 19, 1993Date of Patent: June 17, 1997Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventors: Fumie Sato, Takehiro Amano, Kazuya Kameo, Tohru Tanami, Masaru Mutoh, Naoya Ono, Jun Goto
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Patent number: 5625083Abstract: The present invention relates to novel dinitroglycerol esters of fatty acids, hydroxy fatty acids and prostaglandins, and methods for producing them. Dinitroglycerol esters provided by this invention have an improved biological specificity and/or a greater specific activity than the parent compound. The novel prostanoids produced herein may be used as vasodilators, antihypertensive cardiovascular agents, bronchodilators, and they may have uses in obstetrics and gynecology. The dinitroglycerol esters of fatty acids and hydroxy fatty acids may be useful as platelet antiaggregating agents.Type: GrantFiled: June 2, 1995Date of Patent: April 29, 1997Inventors: Vladimir V. Bezuglov, Igor V. Serkov
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Patent number: 5625067Abstract: The invention relates to cyclopentane ether derivatives of Formula I ##STR1## their salts with physiologically compatible bases, as well as the .alpha.-, .beta.- or .gamma.-cyclodextrin clathrates, and also the liposome-encapsulated compounds of Formula I, processes for their production, and their pharmaceutical usage.Type: GrantFiled: December 14, 1994Date of Patent: April 29, 1997Assignee: Schering AktiengesellschaftInventors: Hartmut Rehwinkel, Ulrich Klar, Helmut Vorbruggen, Karl-Heinz Thierauch, Peter Verhallen
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Patent number: 5618970Abstract: Compounds of formula ##STR1## where R is 5-indanyl or a carboxylic acid protecting group, or an amine salt thereof, are prepared by hydrogenating an (E)-allylic ether of formula ##STR2## in the presence of a stereoselective rhodium or ruthenium biphosphine catalyst and a protic solvent.Type: GrantFiled: March 7, 1996Date of Patent: April 8, 1997Assignee: Pfizer Inc.Inventor: Stephen Challenger
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Patent number: 5618959Abstract: A process for synthesizing prostaglandin E.sub.1, E.sub.2 and derivatives thereof is provided. The process is a "one-pot" method in which 2-furyllithium, copper cyanide, a lower alkyllithium reagent and either an (E)-alkenylstannane or a halogenide are combined with cyclopentenone (II) ##STR1## in which A, R.sup.6 and R.sup.7 are as defined herein. The reaction gives rise to the desired prostaglandin product in yields of 80% or higher.Type: GrantFiled: March 10, 1995Date of Patent: April 8, 1997Assignee: Vivus IncorporatedInventors: Miroslav Trampota, Bohumil Zak
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Patent number: 5610188Abstract: Compounds of the formula ##STR1## wherein the variables are defined in the specification. The compounds and their salts are soft anticholinergic/antisecretory agents especially useful as mydriatics and as antiperspirants.Type: GrantFiled: December 30, 1994Date of Patent: March 11, 1997Assignee: University of FloridaInventors: Richard H. Hammer, Nicholas S. Bodor
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Patent number: 5599838Abstract: A prostaglandin derivative represented by the formula: ##STR1## wherein X is halogen atom R.sup.1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R.sup.2 is a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkylmethyl group having 4 to 10 carbon atoms or a cycloalkylethyl group having 5 to 12 carbon atoms, or a salt thereof, which has an excellent lowering action of intraocular pressure and improving actions of renal diseases, ischemic heart diseases and heart failure.Type: GrantFiled: February 23, 1996Date of Patent: February 4, 1997Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventors: Fumie Sato, Takehiro Amano, Kazuya Kameo, Tohru Tanami, Masaru Mutoh, Naoya Ono, Jun Goto
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Patent number: 5599837Abstract: The present invention relates to a 15-deoxyprostaglandin derivative of the formula (I): ##STR1## in which ##STR2## is a 5 membered ring which is selected from a group consisting of ##STR3## R.sup.1 is hydrogen or lower alkyl; R.sup.2 is C.sub.6 -C.sub.12 alkyl, C.sub.6 -C.sub.12 alkenyl or C.sub.6 -C.sub.12 alkadienyl;provided that the compound of the following formula is excluded: ##STR4## wherein R' is hydrogen or methyl; or pharmaceutically acceptable salts thereof. The invention also relates to a pharmaceutical formulation comprising a 15-deoxyprostaglandin derivative as an active ingredient, which is useful as an intraocular pressure reducing agent.Type: GrantFiled: February 28, 1995Date of Patent: February 4, 1997Assignee: Shionogi & Co., Ltd.Inventors: Morio Kishi, Kimio Takahashi, Kenji Kawada, Yasumasa Goh
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Patent number: 5591887Abstract: 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: December 22, 1994Date of Patent: January 7, 1997Assignee: R-Tech Ueno, Ltd.Inventors: Ryuzo Ueno, Ryuji Ueno
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Patent number: 5583158Abstract: A prostaglandin E.sub.1 analogue represented by formula ##STR1## wherein R.sup.1 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; and X is an oxygen atom and R.sup.2 represents ##STR2## or X is a sulfur atom and R.sup.2 represents ##STR3## The compound has a strong and prolonged inhibitory action for platelet aggregation and is useful for treatment of various thrombotic diseases including peripheral circulatory disturbance.Type: GrantFiled: April 19, 1995Date of Patent: December 10, 1996Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Fumie Sato, Takehiro Amano, Kazuya Kameo, Tohru Tanami, Masaru Mutoh, Naoya Ono, Jun Goto
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Patent number: 5571936Abstract: Intermediate compounds represented as formula (I) useful for the synthesis of 16-phenoxy-prostatrienoic acid derivatives and a preparing method thereof are disclosed. ##STR1## wherein R is tetrahydropyranyl, tetrahydrofuranyl, 2-ethoxyethyl, 3-t-butyldimethylsilyl triisopropylsilyl or triethylsilyl group; R.sup.1 and R.sup.2 are independently hydrogen or ester-forming group; P is hydrogen, trimethylsilyl or tri-n-butyltin; and wavy line means epistereoisomeric mixture.Type: GrantFiled: September 30, 1994Date of Patent: November 5, 1996Assignee: Korea Institute of Science and TechnologyInventors: Hokoon Park, Sun Ho Jung, Yong Sup Lee, Ki Hong Nam
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Patent number: 5569778Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.Type: GrantFiled: April 28, 1995Date of Patent: October 29, 1996Assignee: Daikin Industries Ltd.Inventors: Teruo Umemoto, Ginjiro Tomizawa
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Patent number: 5545665Abstract: The invention relates to 7-[5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxycyclopentyl(enyl)] heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.Type: GrantFiled: December 28, 1993Date of Patent: August 13, 1996Assignee: AllerganInventor: Robert M. Burk
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Patent number: 5543076Abstract: The chiral group of the formula ##STR1## is used as a constituent of liquid-crystalline compounds.Type: GrantFiled: September 16, 1994Date of Patent: August 6, 1996Assignee: BASF AktiengesellschaftInventors: Karl Siemensmeyer, Carsten Tschierske, Fritz Theil, Detley Joachimi
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Patent number: 5534547Abstract: The present invention provides novel prostaglandins D, that is, 13,14-dihydro-15-keto-PGDs, whieh have an excellent sedative and sleep-inducing activity, and so they are useful for tranquilizer and/or soporifics.Type: GrantFiled: September 23, 1994Date of Patent: July 9, 1996Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5523461Abstract: The present invention provides a method of stabilizing a prostanoic acid compound, wherein the prostanoic acid compound having at least one oxo group on the .omega. chain are stored in a hydrous condition.Type: GrantFiled: February 25, 1994Date of Patent: June 4, 1996Assignee: R-Tech Ueno, Ltd.Inventors: Ryuji Ueno, Ryu Hirata
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Patent number: 5516796Abstract: Thiosubstituted prostaglandin derivatives and related compounds having the general structure ##STR1## useful as intraocular pressure reducing agents; pharmaceutical compositions containing such compounds; and methods of treatment using such compositions are disclosed.Type: GrantFiled: March 24, 1994Date of Patent: May 14, 1996Assignee: Kabi Pharmacia ABInventors: Johan W. Stjernschantz, Bahram Resul, Laszlo Z. Bito
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Patent number: 5491254Abstract: ObjectNovel PG derivatives having an excellent platelet aggregation inhibition activity are provided.ConstructionProstaglandin derivatives represented by formula: ##STR1## and salts thereof.Type: GrantFiled: January 19, 1995Date of Patent: February 13, 1996Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventors: Fumie Sato, Takehiro Amano, Kazuya Kameo, Tohru Tanami, Masaru Mutoh, Naoya Ono, Jun Goto
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Patent number: 5476872Abstract: Compounds of the formula ##STR1## where the hatched lines indicate alpha (.alpha.) configuration, a solid triangle is used to indicate beta (.beta.) configuration, lines on both sides of a double bond indicate cis (Z) configuration, and lines on opposite sides of the double bond indicate trans (E) configuration; R.sub.1 is alkyl of 1-10 carbons, C.sub.1 -C.sub.10 alkylphenyl, phenyl-C.sub.1 -C.sub.10 alkyl, or alkenyl of 2 to 10 carbons and having 1 to 3 double bonds; R.sub.2 is Z--OR.sub.3, Z--OCOR.sub.3, Z--OCONHR.sub.3, Z--OCOOR.sub.3, Z--NR.sub.4 R.sub.5, Z--NR.sub.4 COR.sub.3, Z--NR.sub.4 SO.sub.2 R.sub.3, Z--COOR.sub.3, Z--CONR.sub.4 R.sub.5, Z--CHO; Z is (CH.sub.2).sub.n where n is 1-6, or Z is an alkenyl group having 2 to 6 carbons and 1 or 2 double bonds, R.sub.3 is H, alkyl of 1-6 carbons, alkenyl of 2 to 6 carbons or phenyl, R.sub.4 and R.sub.5 independently are H or alkyl of 1 to 6 carbons, have ocular hypotensive activity.Type: GrantFiled: October 18, 1993Date of Patent: December 19, 1995Assignee: Allergan, Inc.Inventors: Michael E. Garst, Elizabeth T. Syage, Michael B. Roof, David F. Woodward, Ming Fai Chan
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Patent number: 5457131Abstract: The present invention relates to cyclopentane heptanoic or cyclopentane heptenoic acid, 2-hydrocarbyl sulfonamidomethyl, and derivatives thereof, useful as therapeutic agents. In particular, the therapeutic agents of this invention are useful as ocular hypotensives.Type: GrantFiled: August 18, 1994Date of Patent: October 10, 1995Assignee: Allergan, Inc.Inventor: Steven W. Andrews
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Patent number: 5453464Abstract: This invention provides the use and preparation of certain 2,2'-diacetyl-bisacetoacetates and bis(beta-ketoesters). These compounds are useful in coating formulations as crosslinkers in conjunction with polyester, acrylic and/or other hydroxylated resins to provide coatings that cure at about 100.degree. and 175.degree. C. Certain combinations of these crosslinkers and resins cure at unusually low temperatures and provide films with good combinations of flexibility, hardness and adhesion.Type: GrantFiled: April 28, 1994Date of Patent: September 26, 1995Assignee: Eastman Chemical CompanyInventors: J. Stewart Witzeman, Allen L. Crain
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Patent number: 5449815Abstract: Object: To provide novel prostaglandin E.sub.1 analogues which have more excellent pharmaceutical effects, longer duration of the effects and less side-effects than the prior art prostaglandin E.sub.1 's.Constitution: A PGE.sub.1 analogue represented by the formula: ##STR1## (wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an allyl group, and R.sup.2 is an alkyl group having 3 to 6 carbon atoms, an alkenyl group having 3 to 6 carbon atoms), or a salt thereof.Type: GrantFiled: October 19, 1993Date of Patent: September 12, 1995Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventors: Fumie Sato, Takehiro Amano, Kazuya Kameo, Tohru Tanami, Masaru Mutoh, Naoya Ono, Jun Goto