Chalcogen Attached Indirectly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/443)
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Patent number: 5739166Abstract: A class of terphenyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and halo; or wherein R.sup.2 and R.sup.3 together form --OCH.sub.2 O--; wherein each of R.sup.6 through R.sup.8 is independently selected from hydrido, lower alkyl, halo, lower alkoxy, lower haloalkyl, and lower dialkylamino; or wherein R.sup.6 and R.sup.7 together form --OCH.sub.2 O; and wherein R.sup.12 is selected from lower alkylsulfonyl and aminosulfonyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: November 29, 1994Date of Patent: April 14, 1998Assignee: G.D. Searle & Co.Inventors: David B. Reitz, Jinglin Li, Monica B. Norton
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Patent number: 5665878Abstract: A process for stereoselectively forming N-substituted dihydro-2,3 benzodiazepines which are useful as AMPA receptor antagonists. The process includes an opening reduction step which sets the stereochemistry of the intermediates and the final compounds to the desired enantiomer. The reduction step may be carried out by an enzymatic reduction.Type: GrantFiled: March 28, 1995Date of Patent: September 9, 1997Assignee: Eli Lilly and CompanyInventors: Benjamin A. Anderson, Marvin M. Hansen, David L. Varie, Jeffrey T. Vicenzi, Milton J. Zmijewski
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1,2-ethanediol derivative and salt thereof and cerebral function-improving agent comprising the same
Patent number: 5658904Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.Type: GrantFiled: June 6, 1995Date of Patent: August 19, 1997Assignee: Toyama Chemical Co., Ltd.Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita -
Patent number: 5506270Abstract: This invention provides a method for treating hypothalamic amenorrhea in a non-depressed female mammal by administering to the mammal an effective amount of a hydroxycycloalkanephenethyl amine compound of the following structural formula: ##STR1## in which A is a moiety of the formula ##STR2## wherein the dotted line represents optional unsaturation;R.sub.1 is hydrogen or alkyl;R.sub.2 is alkyl;R.sub.4 is hydrogen, alkyl, formyl, or alkanol;R.sub.5 and R.sub.6 are, independently, hydrogen, hydroxyl, alkyl, alkoxy, alkanoyloxy, cyano, nitro, alkylmercapto, amino, alkylamino, dialkylamino, alkanamido, halo, trifluoromethyl, or taken together, methylene dioxy;R.sub.7 is hydrogen or alkyl; andn is 0, 1, 2, 3, or 4;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: January 30, 1995Date of Patent: April 9, 1996Assignee: American Home Products CorporationInventors: Gertrude V. Upton, Albert T. Derivan, Richard L. Rudolph
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Patent number: 5482971Abstract: This invention is concerned with novel compounds of formula I: ##STR1## which are selective beta.sub.3 -adrenergic agents.Type: GrantFiled: October 1, 1993Date of Patent: January 9, 1996Assignee: American Cyanamid CompanyInventors: Joseph W. Epstein, Gary H. Birnberg, Feng L. Qing
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Patent number: 5420273Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.6 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.Type: GrantFiled: December 23, 1993Date of Patent: May 30, 1995Assignee: Hoffman-La Roche Inc.Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
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Patent number: 5387700Abstract: A process for producing chlorosulfate and sulfamate esters of 2,3:4,5-bis-O-(1-methylethylidene)-.beta.-D-fructopyranose and (1-methylcyclohexyl)methanol is disclosed. The process involves a two step procedure involving in the first step reacting of an alcohol with sulfuryl chloride in the presence of a tertiary or heterocyclic amine base in a solvent selected from the group consisting of toluene, t-butyl methyl ether or tetrahydrofuran to produce a chlorosulfate intermediate, which is preferably stabilized by an aqueous wash and/or treatment with a base, and in the second step reacting of the resulting intermediate with an amine in a solvent selected from the group consisting of t-butyl methyl ether, tetrahydrofuran and lower alkanol.Type: GrantFiled: August 12, 1993Date of Patent: February 7, 1995Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, Lorraine Scott, Kirk L. Sorgi
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Patent number: 5371247Abstract: A potassium salt useful in the production of certain N-substituted alkyl or arylalkyl thionitroethenamines is produced by the reaction of the dipotassium salt of a 2-nitrodithio aliphatic acid such as 2-nitrodithio acetic acid with branched chain primary alkylamines, secondary alkylamines, arylalkylamines or heterocyclic alkylamines such as dimethylamine, pinacolylamine, benzylamine or piperonylamine, thereby converting one only of the KS-groups to an alkylamine group. The resulting monopotassium salt may be alkylated or arylalkylated to produce an N-substituted alkyl or arylalkyl thionitroethenamine. This compound may be reacted with a suitable amine to produce compounds containing the pharmaceutically active grouping --NHC(.dbd.CHNO.sub.2)NHX, wherein X represents an alkyl, arylalkyl or heterocyclic alkyl group.Type: GrantFiled: July 18, 1991Date of Patent: December 6, 1994Assignee: Fine Organics LimitedInventors: Arthur Jackson, Graham Heyes, James I. Grayson, Paul E. Rowney
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Patent number: 5329023Abstract: The invention relates to a method of preparing optically active alcohols which consist substantially (at least 75% e.e.) or entirely of one enantiomer of formula 4 ##STR1## wherein R and A are as defined therein. The method comprises, which maintaining enantiomeric excess, converting an optically active cyanohydrin of formula 1 ##STR2## into optically active protected cyanohydrin of formula 2 ##STR3## converting the protected cyanohydrin of formula 2 into an optically active compound of formula 3 ##STR4## removing the protecting group B.Type: GrantFiled: June 15, 1992Date of Patent: July 12, 1994Assignee: Duphar International Research B.V.Inventors: Johannes Brussee, Arne Van Der Gen
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Patent number: 5294638Abstract: Pharmacologically active compounds corresponding to the general formula I: ##STR1## wherein m represents 1-4,n represents 2-5,R.sup.1 is hydrogen or lower alkyl,R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, andR.sup.3 is hydrogen, lower alkyl, lower alkoxy or halogen, orR.sup.2 and R.sup.3 are linked to adjacent carbon atoms and together form an alkylenedioxy group with 1-2 carbon atoms,R.sup.4 represents a saturated monocyclic or bicyclic hydrocarbon radical derived from terpenes and having 10 or 11 hydrocarbon atoms, andZ represents oxygen, an N--R.sup.5 group, wherein R.sup.5 is lower alkyl, or if R.sup.4 is a dihydronopyl radical, Z may also be sulfur,and their acid addition salts.Type: GrantFiled: January 19, 1993Date of Patent: March 15, 1994Assignee: Kali-Chemie Pharma GmbHInventors: Insa Hell, Ulf Preuschoff, Hermann Kraehling, Samuel David, Ivan Ban, Marie-Odile Christen
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Patent number: 5272144Abstract: Aryloxy- and heteroaryloxy-alkylene derivatives of amines of formula ##STR1## wherein each of A and B is a group of formula (i) to (iii): ##STR2## wherein Y is --O--, --S-- or --NR-- in which R is hydrogen or C.sub.1 -C.sub.6 alkyl; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is independently:a) hydrogen, halogen, hydroxy, cyano or nitro;b) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by halogen,c) C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkylthio;d) C.sub.1 -C.sub.6 alkyl-sulfonyl;e) a substituted amine group --NR.sub.7 R.sub.8 ;f) a --COR.sub.12 group; org) two adjacent groups of R.sub.3, R.sub.4, R.sub.5 and R.sub.6, taken together, form a C.sub.1 -C.sub.4 alkylenedioxy group;each of R.sub.1 and R.sub.2 independently is hydrogen, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by phenyl; or R.sub.1 and R.sub.Type: GrantFiled: June 13, 1991Date of Patent: December 21, 1993Assignee: Farmitalia Carlo Erba s.r.l.Inventors: Piero Melloni, Philippe Dostert, Arturo D. Torre, Alberto Bonsignori
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Patent number: 5194628Abstract: The reaction of 2,2-difluorobenzo-1,3-dioxole with (a) an alkali metal or an alkali metal compound and then (b) a compound R.sup.1 -Z.sup.1 l in which Z.sup.1 is a leaving group, or with an aldehyde produces compounds of formula I ##STR1## wherein R.sup.1 l is --OH, --SH, --CHO, --CN, --COOH, --B(OH).sub.2, --COX, with X being Cl or Br, or is --COOR.sup.2, --SiR.sub.3.sup.2 or --B(OR.sup.2).sub.2, with R.sup.2 being a C.sub.1 -C.sub.12 alcohol moiety without the hydroxy group, wherein R.sup.1 is further --C.sub.n H.sub.2n COOR.sup.2, with n being an integer from 1 to 4, or linear or branched C.sub.1 -C.sub.12 hydroxyalkyl which is unsubstituted or is substituted by --F, --CN, C.sub.1 -C.sub.6 alkoxy, phenyl, fluorophenyl, C.sub.1 -C.sub.4 alkoxy-phenyl, C.sub.1 -C.sub.4 alkylthio-phenyl, C.sub.1 -C.sub.4 alkyl-phenyl, C.sub.1 -C.sub.4 fluoroalkyl-phenyl, nitrophenyl or by cyanophenyl, or wherein R.sup.1 is a benzyl alcohol which is unsubstituted or is substituted by F, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: September 14, 1990Date of Patent: March 16, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Ackermann, Hans-Ruedi Kanel, Bruno Schaub
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Patent number: 5192765Abstract: Amines of the following formula: ##STR1## where the variables are defined in the specification are useful in the treatment of diseases associated with altered motility and/or tone of smooth muscle.Type: GrantFiled: June 6, 1991Date of Patent: March 9, 1993Assignee: Pfizer Inc.Inventors: David Alker, Robert J. Bass, Peter E. Cross
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Patent number: 5153227Abstract: The invention concerns novel pharmaceutical compositions for use in the treatment of certain complications of diabetes and galactosemia and which contain a nitromethane derivative (or its non-toxic salt) as active ingredient. The nitromethane derivatives are inhibitors of the enzyme aldose reductase. Many of the inhibitors are novel and are provided, together with processes for their manufacture and use, as further features of the invention.Type: GrantFiled: February 6, 1989Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventors: Steven P. Brown, Anthony L. Cooper, Jethro L. Longridge, Jeffrey J. Morris, John Preston
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Patent number: 5135947Abstract: The present invention provides 1-phenyl-3-naphthalenyloxypropanamines which are selective inhibitors of serotonin uptake.Type: GrantFiled: August 1, 1990Date of Patent: August 4, 1992Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong, Dennis C. Thompson
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Patent number: 4999378Abstract: Phenylcarboxylic acid derivatives having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each H, halogen, alkyl, haloalkyl, alkanoyl, cycloalkyl, nitro, amino, --O--D--R.sup.5 (D is alkylene, R.sup.5 is H, amino, morpholino, carboxyl, phthalimido, phenyl, epoxy), substituted or unsubstituted phenoxy, substituted or unsubstituted phenylalkylamino, carboxylalkenyl, or both form alkylenedioxy; R.sup.3 is H, --E--R.sup.6 (E is alkylene, R.sup.6 is H, carboxyl, cyano, OH, phenylalkoxy, or halogen-substituted phenyl, or phenylcarbamoyl), --CO--G--R.sup.7 (G is alkylene, R.sup.7 is H, substituted or unsubstituted phenylcarbamoyl), substituted or unsubstituted benzoyl, alkenyl, carbamoyl, phenyl, or halophenyl; R.sup.4 is H or alkyl; A is alkylene, alkylene condensed with cycloalkyl ring, or alkenylene; B is alkylene or alkenylene; l is 0 or 1.Type: GrantFiled: June 20, 1989Date of Patent: March 12, 1991Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Setsuro Fujii, Hiroyuki Kawamura, Shinichi Watanabe
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Patent number: 4988730Abstract: The invention relates to novel diphenylpropylamine derivatives of the general formula (I). ##STR1## R.sup.1 stands for hydrogen or a methyl group; R.sup.2 stands for hydrogen, a methyl or n-decyl group;Z means a phenyl group substituted by R.sup.3, R.sup.4 and R.sup.5, whereinR.sup.3 means hydrogen, fluorine, chlorine or bromine, or a nitro, C.sub.1-12 alkyl, C.sub.1-4 alkoxy, phenoxy or benzyloxy group;R.sup.4 and R.sup.5 represent hydrogen, chlorine or a hydroxy, alkoxy, benzyloxy, acetamino or carboxy group; orR.sup.4 and R.sup.5 together form a methylendioxy group;orZ may stand for a 4-methoxynaphtyl or 4-ethoxy-naphthyl group; andR.sup.6 stands for hydrogen or fluorine, with the proviso that each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.6 cannot simultaneously stand for hydrogen, as well as their physiologically acceptable acid addition salts.The invention also relates to a process for the preparation of these compounds and to the pharmaceutical compositions containing these compounds.Type: GrantFiled: July 21, 1989Date of Patent: January 29, 1991Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyar RTInventors: Dezso Korbonits, Pal Kiss, Laszlo Szekeres, Gyula Papp, Gabor Kovacs, Andrea Santane Csutor, Sandor Virag, Eva Udvari, Imre Bata, Katalin Marmarosi nee Kellner, Laszlo Tardos, Peter Kormoczy, Vera Gergely, Zoltan Vargai
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Patent number: 4971981Abstract: Novel substituted 1,3-dioxolan and 1,4-dioxan derivatives of formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 each independently of the others represents hydrogen or C.sub.1 -C.sub.4 -alkyl or, if n=1,R.sub.2 and R.sub.4 together represent one of the radicals ##STR2## R.sub.7 represents hydrogen, halogen, methyl, ethyl, C.sub.1 -C.sub.2 -alkyl substituted by 1 to 5 halogen atoms, methoxy, ethoxy or C.sub.1 -C.sub.2 -alkoxy substituted by 1 to 5 halogen atoms;R.sub.8 represents a halogen, C.sub.1 -C.sub.3 -alkyl, C.sub.1 -C.sub.3 -alkyl substituted by 1 to 7 halogen atoms, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.3 -alkoxy substituted by 1 to 7 halogen atoms, or cyano;U represents a grouping --CH.dbd. or --N.dbd.;X represents --O--, --S-- or --N(R.sub.9)--;Y represents --O--, --S--, --S(O)--, --S(O.sub.2)--, --CH.sub.2 --, --CO-- or --N(R.sub.9)--, whereinR.sub.9 represents hydrogen, C.sub.1 -C.sub.Type: GrantFiled: January 19, 1988Date of Patent: November 20, 1990Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4968717Abstract: Compounds of the formula ##STR1## where R.sup.1 to R.sup.7, m, n and p have the meanings stated in the description, and certain derivatives which are p-substituted in the left-hand phenyl ring, are useful for the treatment of disorders.Type: GrantFiled: May 12, 1989Date of Patent: November 6, 1990Assignee: BASF AktiengesellschaftInventors: Liliane Unger, Manfred Raschack, Verena Baldinger, Ferdinand Dengel, Oskar Ehrmann, Hans J. Treiber, Werner Seitz
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Patent number: 4943591Abstract: The invention provides compounds of the general formula (I) ##STR1## wherein X represents a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain andY represents a bond, or a C.sub.1-4 alkylene, C.sub.2-4 alkenylene or C.sub.2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8;Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms or the groups C.sub.1-3 alkyl, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, C.sub.1-3 alkoxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom, or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O-- or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.Type: GrantFiled: October 14, 1986Date of Patent: July 24, 1990Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor, Ian B. Campbell
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Patent number: 4908386Abstract: The present invention provides compounds of general formula (I) ##STR1## wherein Ar represents an unsubstituted or substituted phenyl gorup;R.sup.1 and R.sup.2 each represents a hydrogen atom or a C.sub.1-3 alkyl group;X represents a bond or a C.sub.1-7 alkylene, C.sub.2-7 alkenylene or C.sub.2-7 alkynylene chain;Y represents a bond or a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain;Q represents a substituted phenyl or pyridyl ring;and physiologically acceptable salts and solvates thereof useful as stimulants of .sub.2 -adrenoreceptors and particularly in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.Type: GrantFiled: December 20, 1988Date of Patent: March 13, 1990Assignee: Glaxo Group LimitedInventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell, David Middlemiss, Charles Willbe
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Patent number: 4880840Type: GrantFiled: June 30, 1987Date of Patent: November 14, 1989Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Axel Ingendoh, Friedrich Berschauer, Anno de Jong, Martin Scheer
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Patent number: 4857651Abstract: This invention provides novel .alpha.-[2,2-di(C.sub.1 -C.sub.4 alkoxy)ethylamino]-.beta.-cyanostyrene and .alpha.-[2,2-di(C.sub.1 -C.sub.4 alkoxy)ethylamino]-.beta.-nitrostyrene compounds that are useful for the preparation of pesticidal arylpyrroles. The invention also provides a method for the preparation of the above-said .beta.-cyanostyrene and .beta.-nitrostyrene compounds.Type: GrantFiled: July 29, 1987Date of Patent: August 15, 1989Assignee: American Cyanamid CompanyInventors: Dale G. Brown, Jack K. Siddens, Robert E. Diehl, Donald P. Wright, Jr.
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Patent number: 4772633Abstract: This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.Type: GrantFiled: February 20, 1986Date of Patent: September 20, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
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Patent number: 4751230Abstract: The invention relates to 2,3-dihydrobenzofuran derivatives of the general formula: ##STR1## in which: each of X.sub.1 and X.sub.2, which are identical or different, represents a hydrogen or halogen atom or an alkoxy radical containing from 1 to 4 carbon atoms,X.sub.3 represents a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms,Y represents a hydrogen atom or a hydroxy radical, each of R.sub.1 and R.sub.2, which are identical or different, represents an alkyl radical having from 1 to 4 carbon atoms,or R.sub.1 represents a methyl radical and R.sub.2 represents a phenylalkyl grouping or a 2-indanyl grouping, each of which may be substituted or unsubstituted,or R.sub.1 and R.sub.2 together form, with the nitrogen atom to which they are attached, a piperazinyl radical, a tetrahydroisoquinolyl radical, a morpholinyl radical or a tetrahydrothienopyridinyl radical.Type: GrantFiled: July 16, 1987Date of Patent: June 14, 1988Assignee: ADIR et CompagnieInventors: Gilbert Lavielle, Yves-Michel Gargouil, Jean-Paul Vilaine
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Patent number: 4730008Abstract: The invention provides compounds of the general formula (I) ##STR1## wherein Ar, R.sup.1, R.sup.2, X, Y and Q are defined in the specification and physiologically acceptable salts and solvates thereof.The compounds have a selective stimulant action at .beta..sub.2 -adrenoreceptors and may be used, inter alia, in the treatment of diseases associated with reversible airways obstruction such as asthma and chronic bronchitis.Type: GrantFiled: January 10, 1986Date of Patent: March 8, 1988Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Harry Finch, Alan Naylor, Lawrence H. C. Lunts, Ian B. Campbell
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Patent number: 4725602Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.Type: GrantFiled: October 24, 1985Date of Patent: February 16, 1988Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4720558Abstract: Process for inverting the configuration of secondary alcohols in which the hydroxyl group is attached to an asymmetric carbon atom, in accordance with which the secondary alcohols are esterified, with inversion of their configuration, by conversion into isourea ethers and reaction of these isourea ethers with carboxylic acids, and the esters are then saponified with retention of the configuration of the secondary alcohols.Type: GrantFiled: March 11, 1986Date of Patent: January 19, 1988Assignee: Bayer AktiengesellschaftInventor: Johannes Kaulen
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Patent number: 4680310Abstract: Tetrahydronaphthalene derivatives of the formula ##STR1## wherein Y, m, n, R and R.sup.1 to R.sup.9 are as set forth herein, are described.These compounds have a pronounced calcium-antagonistic and anti-arrhythmic activity and can accordingly be used as medicaments, especially for the control or prevention of angina pectoris, ischaemia, arrhythmias and high blood pressure. The compounds of formula I can be prepared by the amination of a compound of the formula ##STR2## with a corresponding N-methyl-phenylalkylamine and optional subsequent O-acylation. Compounds of formula II and IV are also described and are within the scope of the invention.Type: GrantFiled: October 10, 1985Date of Patent: July 14, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Urs Hengartner, Henri Ramuz
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Patent number: 4536601Abstract: Optically active N-substituted phenylalaninols of the formula (I): ##STR1## wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenzyl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.Type: GrantFiled: September 23, 1983Date of Patent: August 20, 1985Assignee: Dainippon Pharmaceutical Co., Ltd.Inventors: Masatoshi Tukamoto, Tadahiro Sawayama
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Patent number: 4535159Abstract: The present invention relates to a process for producing novel 1-position amino-derivatives of 1-(3',4'-methylenedioxyphenyl)propane-2-ol having general formula I: ##STR1## where R.sub.1 and R.sub.2 are hydrogen, alkyl having 1 to 2 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or benzyl, with the proviso that R.sub.1 and R.sub.2 are not at the same time hydrogen, cycloalkyl or benzyl and where, R.sub.1 and R.sub.2 taken together with the nitrogen atom to which they are attached form a ring having 5 to 7 bonds, which may contain another heteroatom selected from oxygen or nitrogen which can be substituted by benzyl or hydroxyl, as well as the non-toxic addition salts of such derivatives.Type: GrantFiled: April 30, 1982Date of Patent: August 13, 1985Assignee: Ferrer Internacional, S.A.Inventors: Ernesto Forne, Rafael Foguet, Aurelio Sacristan, Jose A. Ortiz
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Patent number: 4535186Abstract: This invention provides a group of hydroxycycloalkanephenethyl amine antidepressant derivatives of the following structural formula: ##STR1## in which A is a moiety of the formula ##STR2## where the dotted line represents optional unsaturation;R.sub.1 is hydrogen or alkyl;R.sub.2 is alkyl;R.sub.4 is hydrogen, alkyl, formyl or alkanoyl;R.sub.5 and R.sub.6 are, independently, hydrogen, hydroxyl, alkyl, alkoxy, alkanoyloxy, cyano, nitro, alkylmercapto, amino, alkylamino, dialkylamino, alkanamido, halo, trifluoromethyl or, taken together, methylenedioxy;R.sub.7 is hydrogen or alkyl; andn is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 26, 1983Date of Patent: August 13, 1985Assignee: American Home Products CorporationInventors: G. E. Morris Husbands, John P. Yardley, Eric A. Muth
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Patent number: 4490392Abstract: A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is the same as defined above, to give a compound of the formula: ##STR3## wherein R' and Ring A are the same as defined above, and when R' is benzyloxy, if required, further subjecting the compound [I'] to catalytic hydrogenation to give a compound of the formula: ##STR4## wherein Ring A is the same as defined above. The benzylalcohol derivative [I] is useful as an anti-diabetic agent.Type: GrantFiled: July 27, 1978Date of Patent: December 25, 1984Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Muneyoshi Ikezaki, Takeshi Kanno, Hajime Iwai, Masanori Inamasu
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Patent number: 4376780Abstract: Novel phenethylamine derivatives represented by the general formula: ##STR1## wherein R is a lower alkyl group, C.sub.n H.sub.2n is a branched or straight alkylene group, A is a phenyl group unsubstituted or substituted with hydroxy, a lower alkoxy or a lower alkylene dioxy group, and n is an integer from 1 to 4, and pharmacologically acceptable acid addition salts thereof, and bronchdilator containing the same. These bronchdilator have an intense and durable bronchdilating effect and a weak heart stimulating action.Type: GrantFiled: October 16, 1981Date of Patent: March 15, 1983Assignee: Eisai Co., Ltd.Inventors: Noriyasu Hirose, Shigeru Souda
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Patent number: 4372969Abstract: The present invention relates to addition salts of substituted aralkylamines of formula:A--CH.sub.2 --NH--R (I)[wherein A is a 3,4-methylenedioxyphenyl group or an .alpha.-hydroxybenzyl, and R is CH(CH.sub.3).sub.2 or C(CH.sub.3).sub.3 ]It relates also to the method for preparing these salts and to their application as pharmaceuticals and in particular as central nervous system antidepressants.Type: GrantFiled: February 19, 1981Date of Patent: February 8, 1983Assignee: Societe Anonyme Dite: Laboratoire L. LafonInventor: Louis Lafon
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Patent number: 4360690Abstract: 1-Aryl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 represents a hydrogen atom, a cyano radical or an alkyl, alkenyl or alkinyl radical within each case up to 7 carbon atoms, andR.sup.2 represents a phenyl radical which is substituted by halogen and/or optionally halogen-substituted phenoxy, with the proviso that the radical R.sup.2 in total contains at least one fluorine substituent,R.sup.3 and R.sup.4, which can be identical or different, represents a fluorine, chlorine or bromine atom or a methyl radical,R.sup.5 represents a hydrogen or halogen atom or a methyl or methoxy radical, andR.sup.6 represents a hydrogen or halogen atom, a cyano nitro or amino radical or an optionally halogen-substituted radical selected from C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy and C.sub.1 to C.sub.4 alkylthio,or whereinthe two radicals R.sup.5 and R.sup.6 together represent an optionally halogen-substituted C.sub.1 or C.sub.Type: GrantFiled: June 12, 1981Date of Patent: November 23, 1982Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel