Z Contains A Cyclopentyl Or Cyclopentene Ring Patents (Class 514/530)
-
Patent number: 4954524Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2,n is 2, 3, 4, or 5,X is hydrogen or fluorine,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position, D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms, a branched, saturated or a straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms, all of which can optionally be substituted by fluorine atoms,m is 1, 2, or 3,E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are different from each other and are hydrogen or alkyl or 1-5 carbon atoms, or are hydrogen or halogen,R.sub.Type: GrantFiled: April 6, 1989Date of Patent: September 4, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Ekkehard Schillinger, Michael H. Town
-
Patent number: 4952581Abstract: This invention provides a method for treating ocular hypertension or glaucoma in a subject's eye. The method comprises contacting the surface of the eye with an effective intraocular pressure reducing amount of a mixture of an adrenergic blocking agent and a prostaglandin or prostaglandin derivative in an ophthalmically compatible carrier, so as to reduce the intraocular pressure of the eye and maintain such reduced intraocular pressure.This invention also provides a composition for topical treatment of ocular hypertension or glaucoma in the eye of a subject. The composition comprises an effective intraocular pressure reducing amount of a mixture of an adrenergic block agent and a prostaglandin or prostaglandin derivative in an ophthalmically compatible carrier.Type: GrantFiled: December 30, 1988Date of Patent: August 28, 1990Assignee: The Trustees of Columbia University in the City of New YorkInventors: Laszlo Z. Bito, Johan W. Stjernschantz
-
Patent number: 4939171Abstract: Alkyl and alkenyl aryl ether derivatives corresponding to the formula: ##STR1## in which R.sup.1 is a saturated cycloaliphatic C.sub.6 -C.sub.20 alkyl group or a mono- or polyunsaturated, linear, branched or cycloaliphatic C.sub.6 -C.sub.20 alkyl group and R.sup.2 is a C.sub.1 -C.sub.4 hydroxyalkyl group, a C.sub.3 or C.sub.4 hydroxyalkenyl group, a group --COOR.sup.3, --CH.sub.2 --COOR.sup.3, --CH.sub.2 --CH.sub.2 --COOR.sup.3 or --CH.dbd.CH--COOR.sup.3, are suitable as sebosuppressive agents in cosmetic or pharmaceutical preparations for topical application to the hair and to the skin.Type: GrantFiled: November 10, 1988Date of Patent: July 3, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Hinrich Moeller, Norbert Banduhn
-
Patent number: 4937265Abstract: An antidiabetic composition which comprises a 7-thiaprostaglandin E.sub.1 represented by the formula ##STR1## wherein R.sup.1 is hydrogen atom, a straight-chain or branched-chain alkyl group or one equivalent of cation, R.sup.2 is hydrogen atom or methyl group, R.sup.3 is a straight-chain or branched-chain alkyl group or a cycloalkyl group, n is 0 or 1, and the asterisk represents an asymmtric carbon atom, which can be administered orally to exhibit the desired activity.Type: GrantFiled: May 17, 1988Date of Patent: June 26, 1990Assignees: Teijin Limited, Fujisawa Pharmaceutical Company, Ltd.Inventors: Toshio Tanaka, Yukio Motoyama
-
Patent number: 4935446Abstract: The present invention relates to novel isomers of PGAs, PGDs, PGEs, PGFs, 6-keto-PGE.sub.1 s, 6-keto-PGF.sub.1 s, PGI.sub.2 s, 6,9.alpha.-nitrilo-PGI.sub.1 s and 6,9.alpha.-methano-PGI.sub.2 s, having a specific steric configuration, which are replaced by an alkyl (C.sub.1 to C.sub.8)-substituted cycloalkyl (C.sub.4 to C.sub.7) group in 1S,S) form, in 1S,R) form or in cis form at the 15-, 16- or 17-position of the PG skeleton, and, alkyl esters thereof, non-toxic salts thereof, non-toxic acid addition salts thereof and cyclodextrin clathrates thereof, possessing more potent PG-like pharmacological activity than other isomers.Type: GrantFiled: March 30, 1989Date of Patent: June 19, 1990Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Hajimu Miyake, Tadao Okegawa
-
Patent number: 4933367Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.Type: GrantFiled: March 12, 1987Date of Patent: June 12, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
-
Patent number: 4916156Abstract: The present invention relates to aromatic derivatives of the formula: ##STR1## in which: n represents an integer between 2 and 10;R.sub.1 and R.sub.2 are identical or different and represent a cycloalkyl containing 3 to 6 carbon atoms or an alkyl containing from 1 to 6 carbon atoms which is unsubstituted or substituted by a phenyl or benzyl group; orR.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded, form a heterocycle selected from pyrrolidin-1-yl, piperidino, azepin-1-yl, hexamethyleneimino, 4-methylpiperidino, 4-benzylpiperidino, 4-phenylpiperidino, 1,2,3,4-tetrahydroisoquinol-2-yl, morpholino and imidazol-1-yl groups;R.sub.3 represents a hydrogen, a halogen, a methyl or a phenyl;R.sub.4 represents a hydrogen, a halogen or a methyl; or R.sub.3 and R.sub.4, taken together with the benzene ring to which they are bonded, form a naphth-1-yl or naphth-2-yl group;Y represents a direct bond, a methyleneoxy group, a methylenethio group or a vinylene group; andR.sub.Type: GrantFiled: April 6, 1988Date of Patent: April 10, 1990Assignee: SanofiInventors: Madeleine Mosse, Vincenzo Proietto
-
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
-
Patent number: 4902717Abstract: Compounds having thromboxane antagonist activity are of use in the treatment of hormone-dependent neoplasias for example oestrogen-dependent neoplasias. Thromboxane antagonists of particular value are compounds of formula (I) ##STR1## wherein ##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.Type: GrantFiled: September 3, 1986Date of Patent: February 20, 1990Assignee: National Research Development CorporationInventors: Judith Senior, Kay M. Troughton
-
Patent number: 4895842Abstract: A phenylalanine derivative having the formula (I): ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen provided that both R.sup.1 and R.sup.2 are not hydrogen at the same time;C.sub.1 -C.sub.8 alkyl which may be substituted with hydroxy, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkoxy, carbamoyl, sulfamoyl, pyridyl, or phenyl which may further be substituted with nitro, C.sub.1 -C.sub.4 alkoxy, or halogen;C.sub.6 -C.sub.8 cycloalkyl which may be substituted with hydroxy, C.sub.1 -C.sub.4 alkoxy, hydroxylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, or C.sub.1 -C.sub.4 alkyl;phenyl which may be substituted with halogen, nitro, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkylcarbonyl, phenylcarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, carbamoyl, sulfamoyl, amidino, pyridylcarbonyl, or C.sub.1 -C.sub.6 alkyl which may further be substituted with C.sub.1 -C.sub.Type: GrantFiled: September 29, 1986Date of Patent: January 23, 1990Assignees: Shosuke Okamoto, Showa Denko Kabushiki KaishaInventors: Shosuke Okamoto, Yoshio Okada, Akiko Okunomiya, Taketoshi Naito, Yoshio Kimura, Morihiko Yamada, Norio Ohno, Yasuhiro Katsuura, Yumi Seki
-
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
-
Patent number: 4883819Abstract: This invention provides a method for treating hypertension or glaucoma in a subject's eye which comprises contacting the surface of the eye with an effective intraocular pressure reducing amount of one or more prostaglandins selected from the group consisting of prostaglandin A (PGA), prostaglandin B (PGB), prostaglandin C (PGC), derivatives of PGA, PGB, and PGC, conjugates of PGA and conjugated derivatives of PGA, so as to reduce the intraocular pressure of the eye and maintain such reduced intraocular pressure. Also provided is a composition for topical treatment of hypertension or glaucoma in the eye of a subject which comprises an effective intraocular pressure reducing amount of one or more prostaglandins selected from the group consisting of PGA, PGB and PGC, derivatives of PGA, PGB and PGC and conjugates of PGA and an opthalmically compatible carrier.Type: GrantFiled: March 5, 1987Date of Patent: November 28, 1989Assignee: The Trustees of Columbia University in the City of New YorkInventor: Laszlo Z. Bito
-
Patent number: 4882341Abstract: The invention relates to amino substituted propenoates and their use against fungi.Type: GrantFiled: September 9, 1988Date of Patent: November 21, 1989Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Ian T. Kay
-
Patent number: 4876279Abstract: Novel 3-hydroxy-3-methylglutaryl-Coenzyme A(HMG-CoA) reductase inhibitors, which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II) ##STR1## and pharmaceutically acceptable salts of the compound (II) in which Z is hydrogen are disclosed.Type: GrantFiled: May 26, 1988Date of Patent: October 24, 1989Assignee: Merck & Co., Inc.Inventors: Ta J. Lee, William F. Hoffman, Clarence S. Rooney
-
Patent number: 4871756Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.Type: GrantFiled: February 17, 1987Date of Patent: October 3, 1989Assignee: Merck Frosst Canada, Inc.Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
-
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
-
Patent number: 4863961Abstract: This invention encompasses prostaglandins of the formula ##STR1## wherein R represents hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.1 represents hydrogen, vinyl, or lower alkyl having 1 to 4 carbon atoms and the wavy line represents R or S stereochemistry; R.sub.2, R.sub.3, and R.sub.4 are hydrogen or lower alkyl having 1 to 4 carbon atoms or R.sub.2 and R.sub.3 together with carbon Y form a cycloalkenyl having 4 to 6 carbon atoms or R.sub.3 and R.sub.4 together with carbons X and Y form a cycloalkenyl having 4 to 6 carbons. Compounds of this invention have potent gastric antisecretory and cytoprotective properties with unexpectedly lower diarrheogenic side effects.Type: GrantFiled: July 28, 1988Date of Patent: September 5, 1989Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki
-
Patent number: 4851432Abstract: This invention relates to the therapeutic uses of oligomers of 15-dehydroprostaglandin B.sub.1 and oligomers of 16, 16'-dimethyl-15-dehydro PGB.sub.1 and oligomers or other 16 carbon substituted 15-dehydro PGB.sub.1 compounds (hereinafter referred to as oligomers of PGB.sub.1) in tissue ischemia, hyposix and anoxia, (hereinafter referred to collectively as tissue ischemia) and in protecting isolated organs (hearts, kidneys etc.) and cells (whole blood, erythrocytes, platelets, etc.) during in vitro transfer and storage; and as a phamacological agent in abnormal conditions in humans and animals in which alteration in cellular calcium is a mediator in the disease process.Type: GrantFiled: May 21, 1987Date of Patent: July 25, 1989Inventor: Thomas M. Devlin
-
Patent number: 4849451Abstract: A fat emulsion containing a prostaglandin E.sub.1 alkyl ester represented by the general formula ##STR1## wherein R denotes an alkyl group having 1 to 30 carbon atoms. The fat emulsion can be administered intravenously, has a long half-life of its effective ingredient, prostaglandin E.sub.1 alkyl ester, in the living body as well as a focus selectivity.Type: GrantFiled: May 16, 1986Date of Patent: July 18, 1989Assignees: Taisho Pharmaceutical Co., Ltd., The Green Cross CorporationInventors: Yutaka Mizushima, Hironaka Aihara, Susumu Otomo, Kazumasa Yokoyama, Hiroyuki Okamoto, Tadakazu Suyama
-
Patent number: 4847293Abstract: This invention encompasses prostaglandins of the formula ##STR1## wherein R represents hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.1 represents hydrogen, vinyl, or lower alkyl having 1 to 4 carbon atoms and a wavy line represents R or S stereochemistry; R.sub.2, R.sub.3, and R.sub.4 are hydrogen or lower alkyl having 1 to 4 carbon atoms or R.sub.2 and R.sub.3 together with carbon Y form a cycloalkenyl having 4 to 6 carbon atoms or R.sub.3 and R.sub.4 together with carbons X and Y form a cycloalkenyl having 4 to 6 carbons. Compounds of this invention have potent gastric antisecretory and cytoprotective properties with unexpectedly low diarrheogenic side effects.Type: GrantFiled: June 10, 1988Date of Patent: July 11, 1989Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki
-
Patent number: 4840968Abstract: The invention provides novel compounds which can protect (i) organs, such as the brain, spinal cord, heart, lung, liver, kidney, stomach, duodenum and blood vessels, (ii) skin cells, and (iii) circulating cells such as red blood cells and white blood cells from ischemic, physical, chemical and biological injuries either by pre-administation or post-administration. The compounds can also protect red blood cells from malarial parasites. The compounds are synthesized from prostaglandin A.sub.1 or E.sub.1 first by alkaline treatment to form free-acid molecules, and then by converting them to hydrophobic ester-form compounds.Type: GrantFiled: January 25, 1988Date of Patent: June 20, 1989Inventor: Tsuyoshi Ohnishi
-
Patent number: 4839388Abstract: This invention relates to a novel prostacyclin represented by the formula: ##STR1## [wherein R.sup.1 represents --CO.sub.2 R.sup.5 group or --CONR.sup.6 R.sup.7 group; A is(i) --CH.dbd.CH--CH.sub.2 CH.sub.2 -- or(ii) --CH.sub.2 CH.sub.2 --O--CH.sub.2 --;B represents --C.tbd.C-- group; R.sup.2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a phenyl group or a phenoxy group;R.sup.3 represents a hydrogen atom, a methyl group or a vinyl group; R.sup.4 represents a hydrogen atom, an acyl group, a tri(1 to 7 carbon atoms)hydrocarbyl-silyl group or a group forming an acetal bond with an oxygen atom of a hydroxy group; a double bond in the substituent represented by A is E or Z, or a mixture thereof; asymmetric center in the substituent represented by R.sup.Type: GrantFiled: May 18, 1987Date of Patent: June 13, 1989Assignees: Mitsubishi Chemical Industries Limited, Sagami Chemical Research CenterInventors: Masakatsu Sibasaki, Mikiko Sodeoka, Katsuhiko Iseki, Masaki Shinoda, Chiyoko Aoki, Yosio Hayasi, Toshiji Kanayama
-
Patent number: 4837234Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.Type: GrantFiled: July 22, 1986Date of Patent: June 6, 1989Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
-
Patent number: 4837363Abstract: Compounds are described of formula (1) ##STR1## in which n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --, or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is --H, C.sub.1-6 alkyl or C.sub.7-10 phenalkyl,Y substituted or unsubstituted 3-phenoxy-2-hydroxypropyl,and their salts.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.Type: GrantFiled: April 23, 1985Date of Patent: June 6, 1989Assignee: Glaxo Group LimitedInventor: Eric W. Collington
-
Patent number: 4837342Abstract: A prostacyclin analogue having the formula: ##STR1## wherein R.sup.1 is --CO.sub.2 R.sup.5 (wherein R.sup.5 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or one equivalent of a cation), or --CONR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom, form a 5- or 6-membered substituted or unsubstituted hetero ring which may contain a hetero atom other than said nitrogen atom); A is --CH.sub.2 CH.sub.2 CH.sub.2 --, CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 -- or --CH.dbd.CHCH.sub.2 CH.sub. 2 --; B is trans --CH.dbd.CH-- or --C.Type: GrantFiled: February 13, 1987Date of Patent: June 6, 1989Assignees: Sagami Chemical Research Center, Toa Eiyo Ltd.Inventors: Masakatsu Shibasaki, Atsuo Takahashi, Tuyoshi Aoki, Kentaro Kogi, Yozo Nishimiya, Takeshi Nara, Takashi Yamaguchi
-
Patent number: 4833169Abstract: Hydropyridine derivatives of the formula ##STR1## in which R.sub.1 represents carboxy, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl, R.sub.2 represents hydrogen, an optionally etherified or acylated hydroxy group or an optionally acylated amino group, and R.sub.3 represents a radical of the formula R-- (Ia), R--alk.sub.1 -- (Ib) or R'.dbd.alk.sub.2 -- (Ic) in which R represents a benzocycloalkenyl radical having a total of from 8 to 12 ring carbon atoms which is bonded via a saturated carbon atom and which is unsubstituted or is mono- or poly-substituted in the benzo moiety by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, lower alkyl and/or by trifluoromethyl, and/or subsituted in the .alpha.Type: GrantFiled: August 3, 1988Date of Patent: May 23, 1989Assignee: Ciba-Geigy CorporationInventors: Georg von Sprecher, Wolfgang Frostl, Armin Zust
-
Patent number: 4833157Abstract: A therapeutic method for inhibiting gastric secretion in an individual for whom such therapy is indicated is disclosed. The method comprises administering to such an individual an effective inhibitory amount of certain derivatives of 15-deoxy-16-hydroxy-prostaglandin E.sub.1 esters.Type: GrantFiled: January 4, 1988Date of Patent: May 23, 1989Assignee: Miles Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
-
Patent number: 4829091Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordane with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: May 27, 1987Date of Patent: May 9, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr
-
Patent number: 4824857Abstract: Method of treatment of ocular hypertension and glaucoma which comprises administering an effective amount of prostaglandin D.sub.2 -active substance to a subject in need of such treatment.Type: GrantFiled: May 4, 1987Date of Patent: April 25, 1989Assignees: Yasumasa Goh, Research Development Corporation of JapanInventors: Yasumasa Goh, Osamu Hayaishi
-
Patent number: 4822820Abstract: Disclosed is the use of Tri-methyl PG-F.sub.2 a, and its derivatives, such as, 15-acetyl Tri-methyl PG-F.sub.2 a and pharmaceutically acceptable esters thereof in the treatment of glaucoma and intraocular hypertension. Also disclosed are ophthalmic pharmaceutical compositions comprising Tri-methyl PG-F.sub.2 a and its derivatives.Type: GrantFiled: November 24, 1986Date of Patent: April 18, 1989Assignee: Alcon Laboratories, Inc.Inventors: Louis M. DeSantis, Verney L. Sallee
-
Patent number: 4822819Abstract: Disclosed is the use of trimoprostil, and its derivatives, such as, 15-acetyl trimoprostil and pharmaceutically acceptable salts and esters thereof in the treatment of glaucoma and ocular hypertension. Also disclosed are ophthalmic, pharmaceutical compositions comprising trimoprostil and its derivatives.Type: GrantFiled: November 7, 1986Date of Patent: April 18, 1989Assignee: Alcon Laboratories, Inc.Inventors: Louis M. DeSantis, Verney L. Sallee
-
Patent number: 4820728Abstract: This invention encompasses prostaglandins of the formula ##STR1## wherein R represents hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.1 represents hydrogen, vinyl, or lower alkyl having 1 to 4 carbon atoms and the wavy line represents R or S stereochemistry; R.sub.2, R.sub.3, and R.sub.4 are hydrogen or lower alkyl having 1 to 4 carbom atoms or R.sub.2 and R.sub.3 together with carbon Y form a cycloalkenyl having 4 to 6 carbon atoms or R.sub.3 and R.sub.4 together with carbons X and Y form a cycloalkenyl having 4 to 6 carbons. Compounds of this invention have potent gastric antisecretory and cytoprotective properties with unexpectedly low diarrheogenic side effects.Type: GrantFiled: June 30, 1987Date of Patent: April 11, 1989Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki
-
Patent number: 4816484Abstract: A compound of D-phenylalanine derivative for hypoglycemic use, represented by the general formula ##STR1## R.sup.1 is selected from hydrogen, alkyl of 1 to 5 carbon atoms, aryl of 6 to 12 carbon atoms, aralkyl of 6 to 12 carbon atoms, ##STR2## --CH.sub.2 CO.sub.2 R.sup.3, --CH(CH.sub.3)--OCO--R.sup.3, and --CH.sub.2 --OCO--C(CH.sub.3).sub.3 ; R.sup.2 is selected from groups comprising aryl of 6 to 12 carbon atoms, a hetero six-membered ring, a hetero five-membered ring, cycloalkyl, or cycloalkenyl, any of which groups may have one or more substituents; and R.sup.3 is selected from hydrogen and alkyl of 1 to 5 carbon atoms; the salts thereof, and precursors which can be converted thereto in the human or animal body.Some of the compounds are novel per se.Type: GrantFiled: January 21, 1988Date of Patent: March 28, 1989Assignee: Ajinomoto Co., Inc.Inventors: Shigeshi Toyoshima, Yoshiko Seto, Hisashi Shinkai, Koji Toi, Izumi Kumashiro
-
Patent number: 4816472Abstract: 9-amino-19,20-bisnorprostanoic acids are useful for depressing appetite.Type: GrantFiled: September 29, 1986Date of Patent: March 28, 1989Assignee: Istituto Biochemico Italiano Giovanni Lorenzini S.p.A.Inventor: Umberto Valcavi
-
Patent number: 4812457Abstract: Permeability characterized in that the carboxy group at 1-position of the prostaglandin is combined with a cell membrane permeable substance having hydroxy group or amino group through the intermediation of an ester bond to the hydroxy group or an amide bond to the amino group are novel and have improved cell membrane permeability.Type: GrantFiled: January 29, 1988Date of Patent: March 14, 1989Assignees: Research Development Corporation, Masami TsuboshimaInventors: Shuh Narumiya, Osamu Hayaishi, Yoshiharu Kimura, Masami Tsuboshima
-
Patent number: 4789685Abstract: 9-fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and 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 --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.- position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: January 20, 1987Date of Patent: December 6, 1988Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
-
Patent number: 4783480Abstract: A 6-keto-prostaglandin E.sub.1 derivative of the formula: ##STR1## (wherein R.sup.1 represents an amino acid or amino alcohol residue, R.sup.2 represents a single bond or an alkylene group of from 1 to 4 carbon atoms, R.sup.3 represents (i) an alkyl group of from 1 to 8 carbon atoms, (ii) a cycloalkyl group of from 4 to 7 carbon atoms, which may be unsubstituted or substituted by at least one alkyl group of from 1 to 8 carbon atoms or (iii) a phenyl or phenoxy group, which may be unsubstituted or substituted by chlorine, trifluoromethyl or alkyl of from 1 to 3 carbon atoms, provided that when R.sup.2 represents a single bond R.sup.3 does not represent phenoxy)cyclodextrin clathrates thereof and non-toxic salts thereof possess selective cytoprotective activity.Type: GrantFiled: January 28, 1987Date of Patent: November 8, 1988Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hirohisa Wakatsuka, Tadao Okegawa, Yoshinobu Arai
-
Patent number: 4777184Abstract: Prostaglandin derivatives, and specifically derivatives of isocarbacyclin, have an optionally substituted methylene group as a substituent on the .alpha.-carbon atom of the .alpha.-side chain. They have a variety of physiological effects, notably a strong ability to inhibit blood platelet aggregation and a strong anti-ulcer activity.Type: GrantFiled: April 29, 1986Date of Patent: October 11, 1988Assignee: Sankyo Company LimitedInventors: Koichi Kojima, Shigeo Amemiya, Kazuo Koyama, Nobuyoshi Iwata, Takeshi Oshima
-
Patent number: 4769388Abstract: A new series of oligomeric or polymeric compounds having a poly(ester) structure, wherein the monomeric starting materials are 1,10-bis(2-hydroxyethylthio)decane, poly(oxyethyleneglycol)s or poly(oxypropyleneglycol)s and carboxylic acids, the process for the preparation thereof and the therapeutic use thereof.Type: GrantFiled: August 7, 1986Date of Patent: September 6, 1988Assignee: Nuovo Consorzio Sanitario NazionaleInventors: Paolo Ferruti, Giancarlo Scapini
-
Patent number: 4766147Abstract: Novel 5-alkylidene-4-substituted-2-cyclopentenones and 5-(1-hydroxy-aliphatic hydrocarbon)-4-substituted-2-cyclopentenones.These novel cyclopentenones and 5-alkylidene-3-hydroxy-4-substituted cyclopentanones have a pharmaceutical activity for treatment of tumors.Type: GrantFiled: January 29, 1986Date of Patent: August 23, 1988Assignee: Teijin LimitedInventors: Ryoji Noyori, Masanori Fukushima, Seizi Kurozumi, Satoshi Sugiura
-
Patent number: 4751240Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined phenolic nucleus including a phenyl-hydroxynaphthyl; hydroxyphenyl-naphthyl; phenyl-hydroxyindanyl, phenyl-hydroxybenzothienyl or mono-hydroxyphenyl-ethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, wherein R.sup.1 is hydrogen, or alkyl, alkenyl, alkynyl, cycloalkyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxyalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 --or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --(PO)R.sup.2 13 , --S--, --SO--or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.Type: GrantFiled: April 24, 1985Date of Patent: June 14, 1988Assignee: Imperial Chemical Industries PLCInventors: Jean Bowler, Graham C. Crawley, Philip N. Edwards, Alasdair T. Glen, Michael S. Large, Brian S. Tait
-
Patent number: 4742080Abstract: A therapeutic method for producing bronchodilation in an individual for whom such therapy is indicated is disclosed. The method comprises administering to said individual an effective bronchodilation amount of certain derivatives of 15-deoxy-16-hydroxy-prostaglandin E.sub.1 esters.Type: GrantFiled: March 15, 1985Date of Patent: May 3, 1988Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woesner, William G. Biddlecom
-
Patent number: 4740524Abstract: Alpha-halopyruvate oximes of the formula: ##STR1## wherein R, R.sup.1, and X are as defined herein having bactericidal and, fungicidal activity are disclosed.Type: GrantFiled: May 16, 1986Date of Patent: April 26, 1988Assignee: Rohm and Haas CompanyInventor: Adam C. Hsu
-
Patent number: 4734424Abstract: Bicycloheptane substituted amide prostaglandin analogs are provided having the structural formula ##STR1## wherein m is 0 to 4; A is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; n is 1 to 5; Q is --CH.dbd.CH--, --CH.sub.2 --, ##STR2## or a single bond; R is CO.sub.2 H, CO.sub.2 alkyl, CO.sub.2 alkali metal, CO.sub.2 polyhydroxyamine salt, --CH.sub.2 OH, ##STR3## wherein R.sup.4 and R.sup.5 are the same or different and are H, lower alkyl, hydroxy, lower alkoxy or aryl, at least one of R.sup.4 and R.sup.5 being other than hydroxy and lower alkoxy; p is 1 to 4; R.sup.1 is H or lower alkyl; q is 1 to 12; R.sup.2 is H or lower alkyl; and R.sup.3 is H, lower alkyl, lower alkenyl, lower alkynyl, aryl, arylalkyl, lower alkoxy, aryloxy, arylalkyloxy, amino, alkylamino arylamino, arylalkylamino, lower alkyl-S-, aryl-S-, arylalkyl-S-, ##STR4## (wherein n' is 0, 1 or 2), alkylaminoalkyl, arylaminoalkyl, arylalkylaminoalkyl, alkoxyalkyl, aryloxyalkyl or arylalkoxyalkyl.Type: GrantFiled: September 24, 1986Date of Patent: March 29, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: Steven E. Hall, Joyce Reid
-
Patent number: 4732914Abstract: Prostacyclin (PGI.sub.2) analogs having a 6a-carba feature, for example a compound of the formula ##STR1## said analogs having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.Type: GrantFiled: May 14, 1987Date of Patent: March 22, 1988Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
-
Patent number: 4722939Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.Type: GrantFiled: December 4, 1984Date of Patent: February 2, 1988Assignee: USV Pharmaceutical CorporationInventors: Bernard Loev, Howard Jones, Wan-kit Chan
-
4-hydroxy-2-cyclopentenone, process for production thereof, pharmaceutical composition comprising it
Patent number: 4711895Abstract: A 4-hydroxy-2-cyclopentenone represented by the following formula (I) ##STR1## wherein X represents a hydrogen or halogen atom, A represents a hydrogen atom and B represents a hydroxyl group, or A and B are bonded to each other to represent a bond, R.sup.1 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, R.sup.2 represents a substituted or unsubstituted alkyl, alkenyl or alkynyl group having 1 to 10 carbon atoms, and R.sup.3 represents a hydrogen atom or a protective group for a hydroxyl group, provided that R.sup.2 is not a 2-octenyl, 8-acetoxy-2-octenyl or 2,5-octadienyl group. The compounds of formula (I) in which A is hydrogen and B is hydroxyl group are prepared by subjecting a 5-unsubstituted cyclopentenone and an aldehyde to aldol condensation reaction. The compounds of formula (I) in which A and B form a bond is prepared by subjecting the compounds of the formula (I) in which A is hydrogen and B is hydroxyl group to dehydration.Type: GrantFiled: October 22, 1985Date of Patent: December 8, 1987Assignee: Teijin LimitedInventors: Atsuo Hazato, Satsohi Sugiura, Seizi Kurozumi, Ryoji Noyori -
Patent number: 4708954Abstract: Pharmaceutical compositions containing an oxaluric acid derivative of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, is hydrogen; an alkyl group or a cycloalkyl group; or R.sub.1 and R.sub.2 are joined to form a heterocyclic ring with the nitrogen atom to which they are both attached; and R.sub.3 is hydrogen or an alkyl group. These compounds have excellent hypoglycemic effects with low toxcicity and safety.Type: GrantFiled: February 7, 1986Date of Patent: November 24, 1987Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kazuharu Ienaga, Ko Nakamura, Akira Ishii
-
Patent number: 4708963Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, a heterocyclic residue, or NHR.sub.3, wherein R.sub.3 is an acid residue or hydrogen;X is oxygen;A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--;W is free or functionally modified hydroxymethylene or free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D is a straight-chain or branched, saturated or unsaturated aliphatic group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms, 1,2-methylene, 1,1-trimethylene;E is --C.tbd.C-- or --CR.sub.6 .dbd.CH.sub.7 -- wherein R.sub.6 and R.sub.7 are hydrogen or alkyl of 1-5 carbon atoms;R.sub.4 is an aliphatic group, cycloalkyl, optionally substituted aryl, or a heterocyclic group;R.sub.5 is free or functionally modified hydroxy and,when R.sub.Type: GrantFiled: May 28, 1985Date of Patent: November 24, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Norbert Schwarz, Helmut Vorbruggen, Jorge Casals-Stenzel, Ekkehard Schillinger, Michael H. Town
-
Patent number: 4707495Abstract: A method of treating peptic ulcer disease by topical application of a prostaglandin analog is described.Type: GrantFiled: October 28, 1985Date of Patent: November 17, 1987Assignee: Ortho PharmaceuticalInventors: Marvin E. Rosenthale, David A. Shriver, Laurence B. Katz