Cyclopentyl (e.g., Prostoglandins, Etc.) Patents (Class 562/503)
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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: 5945295Abstract: This invention relates to a method to assess food spoilage ex vivo by quantification of prostanoid compounds and their metabolites produced by a noncyclooxygenase free radical catalyzed mechanism.Type: GrantFiled: December 22, 1997Date of Patent: August 31, 1999Assignees: Vanderbilt University, Lipoprotein Diagnostics, Inc.Inventors: L. Jackson Roberts, II, Jason D. Morrow, Eric H. Kuhrts
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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: 5932595Abstract: The present invention relates to compounds of Formula I: ##STR1## that are matrix metalloprotease inhibitors, pharmaceutical compositions containing them, methods for their use and methods of preparing these compounds.Type: GrantFiled: December 18, 1996Date of Patent: August 3, 1999Assignees: Syntex (U.S.A.) Inc., Agouron Pharmaceuticals, Inc.Inventors: Steven Lee Bender, Chris Allen Broka, Jeffrey Allen Campbell, Arlindo Lucas Castelhano, Lawrence Emerson Fisher, Robert Than Hendricks, Keshab Sarma
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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: 5886035Abstract: 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: December 18, 1997Date of Patent: March 23, 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: 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: 5858696Abstract: This invention relates to a method to assess oxidative stress in vivo by quantification of prostaglandin F.sub.2 -like compounds and their metabolites produced by a noncyclooxygenase free radical catalyzed mechanism.Type: GrantFiled: August 18, 1997Date of Patent: January 12, 1999Assignee: Vanderbilt UniversityInventors: L. Jackson Roberts, II, Jason D. Morrow
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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: 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: 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: 5700654Abstract: This invention relates to a method to assess oxidative stress in vivo by quantification of prostaglandin F.sub.2 -like compounds and their metabolites produced by a noncyclooxygenase free radical catalyzed mechanism.Type: GrantFiled: September 12, 1994Date of Patent: December 23, 1997Assignee: Vanderbilt UnversityInventors: L. Jackson Roberts, Jason D. Morrow
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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: 5674900Abstract: Novel terpenoid-type quinones which can be obtained from Pycnanthus spp., processes for obtaining the novel terpenoid-type quinones and methods for their use as hypoglycemic agents, for example, in the treatment of diabetes are described. In a preferred embodiment, the novel terpenoid-type quinones are obtained from the leaves and stems of Pycnanthus angolensis. As agents for the treatment of diabetes, the novel terpenoid quinones are useful for treating insulin-dependent (type I) and/or non-insulin-dependent (type II) diabetes.Type: GrantFiled: August 1, 1995Date of Patent: October 7, 1997Assignee: Shaman Pharmaceuticals, Inc.Inventors: Rosa P. Ubillas, Jolad D. Shivanand, Christopher D. Mendez, Diana M. Fort, Joseph L. Evans, Jian Luo
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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: 5648526Abstract: Object: To produce E-prostaglandins in a high yield and in a short time with suppressed formation of isomers.Structure: A process for preparing E-prostaglandins represented by the formula: ##STR1## (wherein A, R.sup.6 and R.sup.7 represent respectively an arbitrary group which does not participate in the reaction; B represents a vinylene or ethynylene group; and R.sup.4 and R.sup.5 may be the same or different from each other and each represents a hydrogen atom or a protective group of the hydroxyl group) which comprises reacting allyl esters of E-prostaglandins represented by the formula: ##STR2## (wherein R.sup.1 and R.sup.2 may be the same or different from each other and each represents a hydrogen atom or a lower alkyl group; R.sup.3 represents a hydrogen atom, a lower alkyl group, an alkenyl group or an aryl group; and A, B, R.sup.4, R.sup.5, R.sup.6 and R.sup.Type: GrantFiled: July 29, 1994Date of Patent: July 15, 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: 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: 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: 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: 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: 5597938Abstract: A novel process for the production of a compound represented by the formula: ##STR1## wherein Z and Z' each represents a protective group for the hydroxyl group; R.sup.1 represents a hydrogen atom or an alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a group represented by the formula --B--D (in which B is an alkylene group and D is a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group or a cycloalkyl group), a substituted or unsubstituted phenyl group or a substituted or unsubstituted phenoxy group; R.sup.3 and R.sup.4 each represents a hydrogen atom, an alkyl group or an alkoxy group; R.sup.5 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, an amino group, a hydroxyl group or a group represented by a formula --COOR.sup.8 ; R.sup.6 represents a group represented by a formula --COOR.sup.9, a cyano group, a hydroxyl group, a group represented by a formula --OCOR.sup.Type: GrantFiled: August 10, 1995Date of Patent: January 28, 1997Assignees: Taisho Pharmaceutical Co., Ltd., Fumie SatoInventor: Fumie Sato
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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: 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: 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: 5532408Abstract: Provided are .alpha.-chain-modified isocarbacyclins of which the .alpha.-chain is modified with a phenylene group, a cycloalkylene group or a thiophendiyl group, and these .alpha.-chain-modified isocarbacyclins show the activity for inhibiting the DNA synthesis of human smooth muscle cell and are expected to be capable of inhibiting the hypertrophy of a blood vessel.Type: GrantFiled: April 5, 1995Date of Patent: July 2, 1996Assignee: Teijin LimitedInventors: Masahiro Koga, Toshio Tanaka, Takao Fujii, Tsukio Masegi
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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: 5506244Abstract: Disclosed are the compounds of formula I ##STR1## wherein R represents hydrogen, lower alkyl, carbocyclic or heterocyclic aryl-lower alkyl or cycloalkyl-lower alkyl; R.sub.1 represents hydrogen, lower alkyl, cycloalkyl, carbocyclic aryl or heterocyclic aryl, or biaryl; R.sub.3 represents hydrogen or acyl; R.sub.4 represents hydrogen, lower alkyl, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryl-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, biaryl or biaryl-lower alkyl; R.sub.5 represents hydrogen or lower alkyl; or R.sub.4 and R.sub.Type: GrantFiled: June 22, 1994Date of Patent: April 9, 1996Assignee: Ciba-Geigy CorporationInventor: Cynthia A. Fink
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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: 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: 5455234Abstract: Mammalian hair growth is reduced by applying to the skin an inhibitor of a cysteine synthetic pathway enzyme.Type: GrantFiled: March 16, 1994Date of Patent: October 3, 1995Inventors: Gurpreet S. Ahluwalia, Douglas Shander
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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
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Patent number: 5436343Abstract: Compounds of formula (I): ##STR1## in which: R.sub.1 and R.sub.2, which may be identical or different, represent a linear or branched (C.sub.1 C.sub.6) alkyl radical, a substituted or unsubstituted phenyl radical, a pyridyl radical or a thienyl radical, or, with the carbon atom to which they are attached, a substituted or unsubstituted (C.sub.4 -C.sub.7) cycloalkyl ring,R.sub.3 representsa substituted or unsubstituted phenylsulfonyl radical,a linear or branched (C.sub.1 -C.sub.6) alkyl radical,an alkylaminocarbonyl radical,or a linear or branched (C.sub.1 -C.sub.6) acyl radical,R.sub.4 represents any one of the radicals:--CH.dbd.CH--(CH.sub.2).sub.p --CO.sub.2 H or --CH.sub.2 --CH.sub.2 --(CH.sub.2)p--CO.sub.2 Hin which p is equal to 0, 1, 2 or 3, n and m, which may be identical or different, represent 0, 1 or 2,their isomers, enantiomers, diastereoisomers and epimers as well as their addition salts with a pharmaceutically acceptable acid or base.Type: GrantFiled: May 14, 1993Date of Patent: July 25, 1995Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Patrick Hautefaye, Michel Laubie, Tony Verbeuren
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Patent number: 5428062Abstract: 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 28, 1993Date of Patent: June 27, 1995Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5414016Abstract: Leukotriene-B.sub.4 derivatives of formula I ##STR1## are described, in which R.sup.1 means CH.sub.2 OH, CH.sub.3, CF.sub.3, COOR.sup.5, CONR.sup.6 R.sup.7, orR.sup.1 together with R.sup.2 means a carbonyl group,R.sup.4 symbolizes H, C.sub.1 -C.sub.10 alkyl optionally substituted, C.sub.3 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl radical optionally substituted, or a 5-6-membered aromatic heterocyclic ring,A symbolizes a trans, trans-CH.dbd.CH--CH.dbd.CH, a --CH.sub.2 CH.sub.2 --CH.dbd.CH-- or a tetramethylene group,B symbolizes a C.sub.1 -C.sub.10 alkylene group, which optionally can be substituted by fluorine or the group ##STR2## D can mean a direct bond, oxygen, sulfur, --C.tbd.C--, --CH.dbd.CR.sup.6 or together withB can also mean a direct bond, their salts with physiologically compatible bases and their cyclodextrin clathrates.Type: GrantFiled: June 13, 1994Date of Patent: May 9, 1995Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5393924Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.Type: GrantFiled: April 29, 1994Date of Patent: February 28, 1995Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
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Patent number: 5387608Abstract: 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 17, 1993Date of Patent: February 7, 1995Assignee: Allergan, Inc.Inventor: Steven W. Andrews
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Patent number: 5380709Abstract: 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 28, 1993Date of Patent: January 10, 1995Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5335769Abstract: A freeze-drying process which reduces loss of the freeze-dried product comprising adding a liquid solution comprising a solid product dissolved in a solvent to a glass container having its inside surface coated with a silicone material; subjecting the container with the liquid solution therein to acceptable operable freeze-drying conditions to remove the solvent and leave the solid product in the container in the form of a dense compact coherent solid; and sealing the container to maintain the solid product stable over a useful storage shelf life.An article of manufacture comprising a sealed glass container having its inside surface coated with a silicone material and containing an in situ freeze-dried dense compact coherent solid product.Type: GrantFiled: November 5, 1992Date of Patent: August 9, 1994Assignee: Schwartz Pharma AGInventors: Karin Klokkers-Bethke, Wilfried Fischer
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Patent number: 5329035Abstract: A process for producing a 2,3-disubstituted-4-substituted cyclopentanone, an enantiomorph thereof, or a mixture of these in an arbitrary ratio.The process comprises (A) subjecting a 4-substituted-2-cyclopentenone, an enantiomorph thereof, or a mixture of these in an arbitrary ratio, and an organocopper compound to conjugate addition-reaction, and thereafter (B) reacting the resulting enolate intermediate with a halide in the presence of a phenyl organotin compound.Type: GrantFiled: March 29, 1993Date of Patent: July 12, 1994Assignee: Teijin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Toshio Tanaka, Seizi Kurozumi
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Patent number: 5317032Abstract: The present invention relates to cathartics comprising 15-keto-16-halogen-PGs as an essential ingredient without substantive side-effects; the catharic effect is thought mainly caused by an enteropooling effect.Type: GrantFiled: December 30, 1992Date of Patent: May 31, 1994Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Sachiko Kuno, Tomio Oda
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Patent number: 5292754Abstract: The present invention relates to a method for treating hypertension or glaucoma in the eye comprising contacting the surface of the eye with a therapeutic amount of 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 or a pharmaceutically acceptable salt thereof. The invention also relates to a kit for delivery of a topical solution for treatment of glaucoma which comprises (a) container having a solution including a compound of the formula (I), and (b) means for topical delivery of said solution to the eye in a controlled dosage.Type: GrantFiled: September 21, 1992Date of Patent: March 8, 1994Assignee: Shionogi & Co., Ltd.Inventors: Morio Kishi, Kimio Takahashi, Kenji Kawada, Yasumasa Goh
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Patent number: 5284858Abstract: 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-ketoprostaglandins 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: August 6, 1992Date of Patent: February 8, 1994Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo KenkyujoInventors: Ryuzo Ueno, Ryuji Ueno, Ichie Kato, Tomio Oda
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Patent number: 5270473Abstract: This disclosure describes novel compounds, N-[(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: February 16, 1993Date of Patent: December 14, 1993Assignee: American Cyanamid CompanyInventor: David A. Cortes
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Patent number: 5268506Abstract: An .alpha., .beta.-unsaturated carboxylic acid is produced by catalytically reacting an .alpha.-hydroxycarboxylic acid amide of the formula (1), ##STR1## where R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl groups, provided that at least one of R.sub.1 and R.sub.2 is the alkyl group, with water in the presence of a solid acid catalyst containing a high surface area rare earth phosphate anhydride having the monoclinic system structure producible by heating a rare earth phosphate of the hexagonal system structure at 60.degree.-200.degree. C. in a solution of an inorganic acid, an inorganic acid salt and/or an inorganic acid ester where the molar ratio of the inorganic acid component to the rare earth phosphate of the hexagonal system structure is 0.5-400.Type: GrantFiled: March 19, 1993Date of Patent: December 7, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Minato Karasawa, Takeshi Hiraiwa, Sinji Tokunoh, Hiroharu Kageyama, Kanemitsu Miyama, Masamitsu Inomata
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Patent number: 5225591Abstract: The disclosed process relates to a method for preparing 1-cyclopentylalkyl amines, useful in the synthesis of artificial sweeteners, by reducing an azanorbornene in a high-yield one-step reduction of an azanorbornene, wherein the method involves use of a solvent reductant system with catalyst that is compatible with the production of edible food compositions.Type: GrantFiled: July 28, 1992Date of Patent: July 6, 1993Assignee: The Coca-Cola CompanyInventors: James G. Sweeny, Lihong L. D'Angelo