Two Rings Only Patents (Class 562/500)
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Patent number: 6136861Abstract: The present invention relates to compounds of the formula I, as defined in the specification, pharmaceutical compositions containing such compounds the use of such compounds to treat neurological and psychiatric disorders.Type: GrantFiled: September 7, 1999Date of Patent: October 24, 2000Assignee: Pfizer IncInventor: Bertrand Leo Chenard
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Patent number: 6110969Abstract: A .omega.-cycloalkyl-prostaglandin E.sub.2 derivatives of the formula (I) ##STR1## wherein R is carboxy or hydroxymethyl; R.sup.1 is oxo, methylene or halogen atom; R.sup.2 is H, OH or C1-4 alkoxy; R.sup.3 is H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkyl, C2-8 alkenyl or C2-8 alkynyl substituted by 1-3 of substituent selected from halogen atom, C1-4 alkoxy, C3-7 cycloalkyl, phenyl, or phenyl substituted by 1-3 of substituent selected from halogen atom, C1-4 alkyl, C1-4 alkoxy, nitro, trifluoromethyl; n is 0-4; and non-toxic salt thereof, prodrug thereof and cyclodextrin clathrate thereof can strongly bind on EP.sub.2 subtype receptor. Therefore, they are useful for prevention and/or treatment of immune disease (autoimmune disease, organ transplantation, etc.), asthma, abnormal bone formation, neuron cell death, liver damage, abortion, premature birth or retina neuropathy of glaucoma etc.Type: GrantFiled: February 4, 1998Date of Patent: August 29, 2000Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Kousuke Tani, Shuichi Ohuchida
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Patent number: 6103925Abstract: The present invention relates to dimethyl-substituted cyclohexanediene derivatives, to a process for their preparation, to their use as pharmaceuticals and to corresponding pharmaceuticals.Type: GrantFiled: September 22, 1998Date of Patent: August 15, 2000Assignee: Bayer AktiengesellschaftInventors: Klaus Urbahns, Frank Mauler
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Patent number: 6099824Abstract: Compounds which can chelate paramagnetic bi- and trivalent metal ions, their chelates with said metal ions and their use as contrast agents in magnetic resonance imaging (MRI), the compounds having formula (I) ##STR1## wherein R is a --(CH.sub.2).sub.m --O--R.sub.2 group or hydrogen,R.sub.2 is a (C.sub.6 -C.sub.10) aryl, or an alkyl(C.sub.1 -C.sub.5)-aryl(C.sub.6 -C.sub.10) group, substituted or not by a group L corresponding to a OH group or a OR.sub.3 group, wherein R.sub.3 is a linear or branched (C.sub.1 -C.sub.5) alkyl group; or L is NH.sub.2, halogen, COOH or CONR.sub.4 R.sub.5 wherein R.sub.4 and R.sub.5 are independently hydrogen, or a linear or branched (C.sub.1 -C.sub.5) alkyl which can be substituted by 1-6 hydroxy groups and/or 1-6 alkoxy groups,R.sub.1 can have the same meanings as R, independently from it, except for hydrogen,Z is independently OH or OR.sub.6, or NR.sub.4 R.sub.5 wherein R.sub.4 and R.sub.5 are as previously defined, and R.sub.6 is a (C.sub.1 -C.sub.Type: GrantFiled: August 1, 1997Date of Patent: August 8, 2000Assignee: Dibra S.p.A.Inventors: Pier Lucio Anelli, Andrea Beltrami, Fulvio Uggeri, Mario Virtuani
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Patent number: 6040462Abstract: Novel calix[4]arene dibenzo crown ethers useful to selectively extract cesium are represented by the formula: wherein R is a C.sub.1 -C.sub.10 normal alkyl, a phenyl or a methoxyphenyl, R' is hydrogen, p-tert-butyl or a C.sub.1 -C.sub.10 normal alkyl, R" is a C.sub.1 -C.sub.10 normal alkyl, and n is an integer of 0-2. The novel compound is prepared at high yields by introduction of benzene rings into the crown ether ring of calix[4]arene crown-6-ether. The calix[4]arene dibenzo crown ethers are superior in selective absorptivity for cesium ions by virtue of their 1,3-alternate conformational structure and thus, can be used as selective extractants able to separate cesium ions at a high efficiency.Type: GrantFiled: November 23, 1998Date of Patent: March 21, 2000Assignees: Korea Atomic Energy Research Institute, Korea Electric Power CorporationInventors: Won Zin Oh, Kune Woo Lee, Wang Kyu Choi, Hyun Soo Park, Jong Seung Kim, Moon Hwan Cho, Jong Kook Kim
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Patent number: 6020370Abstract: Bridged cyclic amino acids of formula ##STR1## are disclosed and are useful as agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain and neuropathological disorders. Processes for the preparation and intermediates useful in the preparation are also disclosed.Type: GrantFiled: May 19, 1998Date of Patent: February 1, 2000Assignee: Warner-Lambert CompanyInventors: David Christopher Horwell, Justin S. Bryans, Clare O. Kneen, Andrew I. Morrell, Giles S. Ratcliffe
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Patent number: 5912248Abstract: Compounds of the formula ##STR1## in which X represents a bond, S, SO or SO.sub.2 ; and R is as defined in the specification are useful as modulators of metabotropic glutamate receptor function.Type: GrantFiled: November 14, 1996Date of Patent: June 15, 1999Assignee: Eli Lilly and CompanyInventors: Carmen Dominguez Fernandez, James Allen Monn, Matthew John Valli
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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: 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: 5726320Abstract: A process for the preparation of (+)-2-amino-bicyclo?3.1.0!-hexane-2-6-dicarboxylic acid, or a pharmaceutically acceptable salt thereof, which comprises hydrolysing (-)-2-spiro-5'-hydantoinbicyclo?3.1.0!hexane-6-carboxylic acid or a salt thereof, and optionally forming a pharmaceutically acceptable salt. Also disclosed are intermediates useful in the process.Type: GrantFiled: June 26, 1996Date of Patent: March 10, 1998Assignee: Eli Lilly and CompanyInventor: Roger Lewis Robey
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Patent number: 5723494Abstract: Compounds represented by general formula (I) and (II), in which r is 1 or 2, R.sub.2 and R.sub.3 are selected independently from H, CH.sub.3, C.sub.2 H.sub.5 and CHO, provided that R.sub.2 and R.sub.3 are not simultaneously CHO, and in which R.sub.1 is selected from: an aminoalkyl adamantyl group, a monocyclic aminoalkyl group, a dicyclic aminospiro group, a dicyclic amino group (orthofused), a dicyclic amino group, and azacycloalkyl group, an azadicyclic group (orthofused), a dicyclic azaspiro group, and azadicyclic group, and azacycloalkyl group, and a linear or branched aminoalkyl group.Type: GrantFiled: September 11, 1995Date of Patent: March 3, 1998Assignee: Rotta Research Laboratorium S.P.A.Inventors: Francesco Makovec, Walter Peris, Lucio C. Rovati, Luigi A. Rovati
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Patent number: 5686621Abstract: Substituted hydrindanes and their use in controlling angiogenesis-dependent diseases in warm blooded animals are disclosed.Type: GrantFiled: June 6, 1995Date of Patent: November 11, 1997Assignee: Alcon Laboratories, Inc.Inventors: Abbot F. Clark, Raymond E. Conrow
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Patent number: 5639894Abstract: A process for the carbonylation of allylic alcohols such as nerolidol, farnesol, or their monocyclic analogues with carbon monoxide at a pressure of at least 30 bar in the presence of a polar solvent and a palladium halide catalyst, optionally an alkali metal halide salt, and optionally an alcoholic solvent. The carbonylated product may then be reduced to the corresponding alcohol, which is cyclized in the presence of Lewis or Bronsted acids to afford an ambergris fragrance compound.Type: GrantFiled: March 23, 1994Date of Patent: June 17, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Jonathan M. Cassel, Steven M. Hoagland, James M. Renga
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Patent number: 5545666Abstract: A prostaglandin derivative represented by formula ##STR1## wherein R.sup.1 represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group, and R.sup.2 represents a cyclohexyl group or a cyclopentylmethyl group. This compound has physiological activities such as platelet aggregation-inhibiting action, renal blood vessel and coronary blood vessel-dilating actions and the like, and is useful for treatment of renal failure and diseases of circulatory organs.Type: GrantFiled: April 19, 1995Date of Patent: August 13, 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: 5464866Abstract: Substituted hydrindanes and their use in controlling angiogenesis-dependent diseases in warm blooded animals are disclosed.Type: GrantFiled: March 10, 1994Date of Patent: November 7, 1995Assignee: Alcon Laboratories, Inc.Inventors: Abbot F. Clark, Raymond E. Conrow
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Patent number: 5449684Abstract: Compounds isolated from a marine sponge, and derivatives thereof, have the formulae: ##STR1## in which R.sup.1 is H or lower alkyl; R.sup.2 is OH or CH.sub.3 ; R.sup.3 is OH or CH.sup.3, and R.sup.4 H or MPTA. The compounds have antitumor and antiviral activity. The invention also provides pharmaceutical compositions containing the compounds and methods of treatment employing them.Type: GrantFiled: February 3, 1994Date of Patent: September 12, 1995Assignee: PharmaMar, S.A.Inventors: Jun-Ichi Tanaka, Tatsuo Higa, Khanit Suwanoborirux, C. W. Jefford, G. Bernardinelli, Dolores G. Gravalos
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Patent number: 5340828Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: September 30, 1991Date of Patent: August 23, 1994Assignee: Merck & Co., Inc.Inventors: Samuel L. Graham, S. Jane deSolms
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Patent number: 5340835Abstract: A compound selected from the group consisting of all stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein Y and Z are individually selected from the groups consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms and aryl, aryloxy and arylthio of up to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen, hydroxy optionally esterified etherified, --CF.sub.3 and alkyl of 1 to 8 carbon atoms and R is alkyl of 1 to 8 carbon atoms or the remainder of a pyrethrinoid alcohol having excellent pesticidal properties and their preparation and intermediates.Type: GrantFiled: January 19, 1993Date of Patent: August 23, 1994Assignee: Roussel-UCLAFInventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Fabienne Pilorge, Nicole Reinier
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Patent number: 5228898Abstract: This invention relates to substituted bicycloheptadione derivatives with high herbicidal activity which are represented by general formula (I) ##STR1## (where R.sup.1 is a lower alkyl group, a phenyl group which may be substituted, an aralkyl group which may be substituted, or a heterocyclic group which may be substituted;R.sup.2 is, same or different, a halogen, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkyl group, an alkoxyalkyl group, or an alkoxylcarbonyl group, and n is 0 to 4;R.sup.3 and R.sup.4 are, same or different, hydrogen or a lower alkyl group).Type: GrantFiled: February 3, 1992Date of Patent: July 20, 1993Assignee: Nippon Soda Co., Ltd.Inventors: Akiyoshi Ueda, Shigemi Suga, Hiroyuki Adachi, Toshio Aihara, Kazuyuki Tomida, Hideki Yamagishi, Hideo Hosaka
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Patent number: 5177251Abstract: The present invention relates to a novel class of halogenated tetraenyl prostaglandin compounds represented by the following general formula ##STR1##or a pharmaceutically acceptable salt thereof, whereinY is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --;R.sub.1 is H or a lower alkyl of 1 to 6 carbons;n is an integer from 0 to 3;m is an integer from 0 to 3 and n+m=3; X is Cl or F provided that when X is Cl, n is 2 and m is 1;R.sub.2 and R.sub.3 are independently H, lower alkyl from 1 to 6 carbons, Cl, --CH.sub.2 Cl, --CH.sub.2 F, --CHCl.sub.2, --CCl.sub.3, or taken together form a cycloalkyl of 3 to 6 carbons;R.sub.4 is H, lower alkyl from 1 to 6 carbons, Cl, F or taken together with R.sub.3 form a cycloalkenyl of 4 to 6 carbons; and provided that at least one of --CH.sub.n X.sub.m, R.sub.2, R.sub.3 and R.sub.4 includes a chlorine or fluorine atom.Type: GrantFiled: December 24, 1991Date of Patent: January 5, 1993Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Steven W. Kramer, Robert L. Shone
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Patent number: 5177109Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.Type: GrantFiled: July 19, 1991Date of Patent: January 5, 1993Assignee: G. D. Searle & Co.Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
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Patent number: 5142099Abstract: An enantioselective process for the preparation of hemicaronic aldehyde with a cis or trans structure and novel intermediates.Type: GrantFiled: November 13, 1991Date of Patent: August 25, 1992Assignee: Roussel UclafInventor: Alain Krief
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Patent number: 5130468Abstract: A process and intermediates useful for the preparation of (E)-alkene dipeptide isosteres are disclosed.Type: GrantFiled: May 9, 1991Date of Patent: July 14, 1992Assignee: Abbott LaboratoriesInventor: Dale J. Kempf
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Patent number: 5117042Abstract: A method of treatment for improving encephalic function which comprises administering, to a subject in need of such treatment, a 15-keto-prostaglandin compound in an amount effective for improvement of encephalic function.Type: GrantFiled: November 21, 1990Date of Patent: May 26, 1992Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuji Ueno, Hiroyoshi Osama, Tomio Oda
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Patent number: 5095137Abstract: The amides of cyclomethylen-1,2-bicarboxylic acids having the formula: ##STR1## wherein A represents ##STR2## R.sup.1 represents --H, --CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, ##STR3## R.sup.2 represents --H, CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --C.sub.6 H.sub.5, --C.sub.6 --H.sub.5 ;R.sup.3 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, ##STR4## R.sup.5 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 C.sub.6 H.sub.5, ##STR5## Y=--H, --CH.sub.3, --CH(CH.sub.3).sub.2 Z=--H,--CH.sub.3, --C(CH.sub.3).sub.3, --CH(C.sub.2 H.sub.5).sub.2, ##STR6## R.sup.4 =R.sup.5, ##STR7## m is 0 or 1 and n is an integer varying between 0 and 3, are endowed with ACE-inhibiting activity and are thus therapeutically useful as anti-hypertension agents.Type: GrantFiled: October 9, 1990Date of Patent: March 10, 1992Assignee: Laboratori Guidotti SpAInventors: Luigi Turbanti, Guido Cerbai, Marco Criscuoli
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Patent number: 5089524Abstract: Tetraenyl Prostanoic Acid derivatives which are useful as prodrugs for the treatment of peptic ulcer disease and are represented by the following general formula ##STR1## are disclosed.Type: GrantFiled: June 28, 1990Date of Patent: February 18, 1992Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki
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Patent number: 5081282Abstract: Bicyclo prostaglandin analogues have been prepared.Type: GrantFiled: January 13, 1988Date of Patent: January 14, 1992Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5077309Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.Type: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5043451Abstract: There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkylamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 --O--CH.sub.2 --or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically acceptable salts. The compounds are useful as antithrombotic, anti-vasoconstricting and anti-bronchoconstricting drugs.Type: GrantFiled: April 27, 1990Date of Patent: August 27, 1991Assignee: Shionogi & Co., Ltd.Inventors: Mitsuaki Ohtani, Fumihiko Watanabe, Tadadiko Tsushima, Kenji Kawada, Susumu Kamata
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Patent number: 5036104Abstract: 2-Acylaminoalkyl-3-[1-(carboxycycloalkylcarbamoyl)cycloalkyl]propanoic acid derivatives (which may also be viewed as glutaramide derivatives) are useful in the treatment of hypertension, heart failure and renal insufficiency, based upon their inhibition of zinc-dependent, neutral endopiptidase.Type: GrantFiled: June 14, 1990Date of Patent: July 30, 1991Assignee: Pfizer Inc.Inventors: John C. Danilewicz, Keith James
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Patent number: 5025017Abstract: Seco-mevinic acid derivatives are provided which has the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.Type: GrantFiled: September 28, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5004752Abstract: The invention relates to 9-halo-15-cycloalkyl prostaglandin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.2 is fluorine or chlorine,n is 0 or 1,and, if R.sub.1 is hydrogen, the salts thereof with physiologically compatible bases or the cyclodextrin clathrates thereof, processes for their preparation, and their pharmaceutical usage.Type: GrantFiled: May 8, 1989Date of Patent: April 2, 1991Assignee: Schering AktiengesellschaftInventors: Bernd Raduechel, Werner Skuballa, Helmut Vorbrueggen, Olaf Loge, Ekkehard Schilliner
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4975444Abstract: Compounds of the formula ##STR1## wherein A is a carbocyclic, saturated or unsaturated ring; R.sup.1 is hydrogen or alkyl; R and R.sup.4 are each alkyl, cycloalkyl, benzyl or a readily hydrolyzable ester group; Y is a bond or a straight or branch alkylene; R.sup.2 is hydrogen, aryl, heterocyclic, R.sup.6 CONR.sup.5, R.sup.7 NR.sup.5 CO, R.sup.7 NR.sup.5 SO.sub.2 --or R.sup.8 SO.sub.2 NR.sup.5 --where R.sup.5 is hydrogen, alkyl or aralkyl; R.sup.6 is alkyl, aryl, aralkyl, heterocyclic, heterocyclyalkyl or a group of the formula ##STR2## where R.sup.9 is hydrogen, hydroxy, alkoxy, alkyl, hydroxyalkyl, aralkyl, alkylene, heterocyclic, heterocyclylalkyl, R.sup.12 CONH--, R.sup.12 SO.sub.2 NH-- or (R.sup.13).sub.2 N--; R.sup.10 and R.sup.11 are each hydrogen or alkyl; or R.sup.10 is hydrogen and R.sup.11 is aminoalkyl, imidazolylmethyl, aryl, aralkyl, aralkoxyalkoxy, hydroxyalkyl or methylthioalkyl; or R.sup.10 and R.sup.Type: GrantFiled: August 25, 1989Date of Patent: December 4, 1990Assignee: Pfizer Inc.Inventors: John C. Danilewicz, Keith James, Ryszard J. Kobylecki
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Patent number: 4965279Abstract: Novel cyclopropyl aza prostaglandin analogs are disclosed having the formula ##STR1## wherein A can be carbonyl, sulfonyl or a single bond. These compounds are useful, for example, as thromboxane antagonists.Type: GrantFiled: November 18, 1988Date of Patent: October 23, 1990Assignee: E. R. Squibb & Sons, Inc.Inventors: Raj N. Misra, David M. Floyd, Steven E. Hall
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Patent number: 4960792Abstract: 2-Acylaminoalkyl-3-[1-(carboxycycloalkylcarbamoyl)cycloalkyl]propanoic acid derivatives (which may also be viewed as glutaramide derivatives) are useful in the treatment of hypertension, heart failure and renal insufficiency, based upon their inhibition of zinc-dependant, neutral endopiptidase.Type: GrantFiled: May 8, 1989Date of Patent: October 2, 1990Assignee: Pfizer Inc.Inventors: John C. Danilewicz, Keith James
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Patent number: 4957940Abstract: Certain bicyclo [2.2.1] heptane and bicyclo [2.2.2] octane substituted tetrahydro-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.Type: GrantFiled: November 21, 1989Date of Patent: September 18, 1990Assignee: Warner-Lambert CompanyInventor: Bruce D. Roth
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Patent number: 4945106Abstract: Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.Type: GrantFiled: July 6, 1989Date of Patent: July 31, 1990Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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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
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Patent number: 4918223Abstract: N-acylated mercapto-.alpha.-amino acids of the general formula ##STR1## are prepared by reacting a nitrile of the general formulaR.sub.1 -CN (II)at a temperature between 0.degree. C. and 100.degree. C. in water or in a mixture of water and an organic solvent which is at least partially miscible with water, in the presence of a base with a mercapto-.alpha.-amino acid of the general formula ##STR2## and subsequently releasing the N-acylated mercapto-.alpha.-amino acid of general formula (I) with an acid. Mercapto-.alpha.-amino acids can be selectively acylated on the amino group in this manner in a relatively simple manner.Type: GrantFiled: August 9, 1988Date of Patent: April 17, 1990Assignee: Degussa AktiengesellschaftInventors: Hans-Peter Krimmer, Karlheinz Drauz
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4897379Abstract: The invention relates to N-[N.sup..alpha. -(1(S)-carboxy-3-cyclohexylpropyl)-L-lysyl]-N-cyclopentylglycine which is useful as antihypertensives.Type: GrantFiled: March 24, 1988Date of Patent: January 30, 1990Assignee: Asahi Breweries Ltd.Inventors: Shizuo Saito, Motoshi Watanabe, Shuji Fukushima, Shinichi Matsui
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Patent number: 4892965Abstract: 3,3'-Thiobis(2,5-dihydrothiophene-1,1-dioxides) on heating with a reactive Diels-Alder dienophile undergo a reaction producing thioethers having two six-membered alicyclic rings in the molecule, such as 4,4'-thiobis(3,6-dihydrophthalic acids) of the esters, anhydrides or imides thereof, and 4,4'-thiobis(1,2,3,6- tetrahydrophthalic adics) or the esters, anhydrides or imides thereof. Both rings of the dihydrothiophene dioxides participate in the reaction, apparently by forming a tetraene structure which co-reacts with two equivalents of the dienophile to form an adduct in which each six-membered ring has one or two olefinic double bonds. During the course of the reaction, the thioether bridge remains intact. Some of the bis(alicyclic) thioethers are readily converted to the corresponding bis(aromatic)thioethers by use of known aromatization methods and systems. Various utilities for the products of the foregoing reactions are described.Type: GrantFiled: June 6, 1988Date of Patent: January 9, 1990Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4888358Abstract: Novel 13,14-dihydroprostaglandin derivatives of the formula ##STR1## wherein: m is 1 or 3;R.sub.1 is hydrogen or alkyl;R.sub.2 is hydrogen or lower alkyl;R.sub.3 and R.sub.4 are independently hydrogen or methyl;R.sub.5 is alkyl, CF.sub.3 (CH.sub.2).sub.n -- in which n is an integer of 3-5, cycloalkyl, or optionally substituted phenyl, benzyl or phenoxy; orR.sub.4 and R.sub.5 taken together with the carbon to which they are attached is cycloalkyl of 4-8 carbon atoms;X is cis --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 -- when m is 3, orX is --CH.sub.2 CH.dbd.C.dbd.CH-- when m is 1;and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.;or a pharmaceutically acceptable salt thereof,have been prepared. They are useful in particular for their antihypertensive and anti-ulcerogenic properties.Type: GrantFiled: August 25, 1988Date of Patent: December 19, 1989Assignee: Syntex (U.S.A.) Inc.Inventors: Joan Huguet, Joseph M. Muchowski, Maria T. Lara
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Patent number: 4861913Abstract: Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or heterocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms an may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.Type: GrantFiled: November 5, 1986Date of Patent: August 29, 1989Assignee: Shionogi & Co., Ltd.Inventors: Masayuki Narisada, Mitsuaki Ohtani, Fumihiko Watanabe, Sanji Hagishita, Kaoru Seno, Susumu Kamata, Nobuhiro Haga, Tatsuo Tsuri, Tadahiko Tsushima, Kenji Kawada
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Patent number: 4851035Abstract: An ethylene biosynthesis inhibitor is provided comprising 2-cycloalkyl-1-aminocyclopropanecarboxylic acids or a derivative thereof. By applying the subject compound in an ethylene-production-inhibiting amount, ripening and senescence can be slowed. The compound finds use in conjunction with the inhibition of ripening and improved storage of fruits, vegetables and cut flowers.Type: GrantFiled: May 1, 1986Date of Patent: July 25, 1989Assignee: The Board of Trustees of the Leland Stanford Junior University, Stanford UniversityInventors: Michael C. Pirrung, Gerald M. McGeehan
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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
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Patent number: 4845282Abstract: The present invention provides an industrially very advantageous process for producing prostaglandins E.sub.1 with fewer steps and in higher yield. The process comprises reacting a 7-hydroxyprostaglandin E with a reactive derivative of an organic sulfonic acid in the presence of a basic compound to form the corresponding 7-organic sulfonyloxyprostaglandin E, treating the resulting 7-organic sulfonyloxyprostaglandin E, after or without isolation, in the presence of a basic compound to form a .DELTA..sup.7 -prostaglandin E, thereafter selectively reducing the carbon-carbon unsaturated bond existing on the .alpha.-chain. Some of the 7-hydroxyprostaglandins E and .DELTA..sup.7 -prostaglandins E used in the process are novel compounds.Type: GrantFiled: January 21, 1988Date of Patent: July 4, 1989Assignee: Teijin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Toshio Kawagishi, Seizi Kurozumi
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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
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Patent number: 4833271Abstract: Structurally-defined, low molecular weight oligomers and preparation thereof which are active in the protection of oxidative physphorylation of mitochondria and exhibit ionophoretic activity. Said structurally defined low molecular weight oligomers are synthesized using a modified 15-dehydro PGB.sub.1 such as 16,16-dimethyl-15-dehydro prostaglandin B.sub.1 as a precursor to obtain oligomeric mixtures which are structurally defined and active in the protection of oxidative phosphorylation and exhibit ionophoretic activity. Synthesis of modified 15-dehydro-PGB.sub.1 ; 16,16-dimethyl-15-dehydro-prostagalandin B.sub.1 ; is also described.Type: GrantFiled: August 23, 1985Date of Patent: May 23, 1989Inventor: George L. Nelson