Halogen Bonded Directly To The Aryl Ring Oring System Patents (Class 564/351)
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Patent number: 7807854Abstract: To provide a medicament which efficiently expresses an immunosuppressive agent or an anti-inflammatory agent and reduces expression of side effect. A medicament includes diaryl sulfide or diaryl ether compound having a 2-amino-1,3-propanediol structure having an activity of reducing lymphocytes circulating peripherally, in combination with an immunosuppressive agent and/or an anti-inflammatory agent.Type: GrantFiled: December 31, 2009Date of Patent: October 5, 2010Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Shinji Kudou, Kazuhiko Kuriyama, Tokutarou Yasue
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Patent number: 7781617Abstract: A medicine which effectively functions as an immunosuppressant or anti-inflammatory agent and is effective in diminishing the occurrence of side effects. The medicine comprises a combination of: a diaryl sulfide or diaryl ether compound having a 2-amino-1,3-propanediol structure and having the function of diminishing lymphocytes circulating through the periphery; and an immunosuppressant and/or an anti-inflammatory agent.Type: GrantFiled: July 15, 2005Date of Patent: August 24, 2010Assignee: Kyorin Pharmaceutical Co., LtdInventors: Shinji Kudou, Kazuhiko Kuriyama, Tokutarou Yasue
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Patent number: 7763752Abstract: An amino alcohol derivative represented by the following general formula (1) (for example, (±)-2-amino-5-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-2-methylpentane-1-ol) exhibits strong immunosuppressive effect while causing less side effects: .Type: GrantFiled: November 21, 2008Date of Patent: July 27, 2010Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Yasushi Kohno, Kiyoaki Tanaka, Kazuhiko Kuriyama
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Patent number: 7482491Abstract: An amino alcohol derivative represented by the following general formula (1) (for example, (±)-2-amino-5-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-2-methylpentane-1-ol) exhibits strong immunosuppressive effect while causing less side effects:Type: GrantFiled: September 16, 2003Date of Patent: January 27, 2009Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Yasushi Kohno, Kiyoaki Tanaka, Kazuhiko Kuriyama
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Patent number: 7368608Abstract: An 1-amido-3-(2-hydroxyphenoxy)-2-propanol derivative represented by the following formula (1), wherein cycle A may have further 1 to 4 substituents, and said substituent means a substituent selected from the group consisting of saturated or unsaturated C1-4 alkyl group, aralkyl group in which alkyl moiety has 1 to 4 carbon atoms, aryl group, halogen atom, halogenated C1-4 alkyl group, C2-5 alkanoyl group, mono or dialkylcarbamoyl group in which alkyl moiety has 1 to 4 carbon atoms, cyano group and nitro group, and the substituents at positions 3 and 6, or at positions 4 and 5 on the cycle A are different each other. Other ring may be fused at positions 3 and 4, or at positions 5 and 6 on the cycle A to form a condensed polycyclic hydrocarbon with the cycle A. R1 is alkanoyl group or aroyl group, and R2 is hydrogen atom, alkanoyl group or aroyl group, or R1 and R2 may be combined together with the N atom to form a cyclic imido group, which is useful as an intermediate of medicines, etc.Type: GrantFiled: July 19, 2005Date of Patent: May 6, 2008Assignee: Daiso Co., Ltd.Inventors: Yasushi Miki, Masafumi Mikami
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Patent number: 7030160Abstract: The invention relates to phenoxypropanolamines, to pharmaceutical compositions containing them, to processes for preparing them, and to the method of use thereof in the treatment of diseases that are improved by beta-3 agonist action.Type: GrantFiled: May 29, 2001Date of Patent: April 18, 2006Assignee: Sanofi-AventisInventors: Laura Barzaghi, Philippe R. Bovy, Roberto Cecchi, Tiziano Croci, Stefano Romagnano
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Patent number: 6963012Abstract: The present invention provides diaryl ether derivatives that exhibit significant immunosuppressive effects with less side effects. The diaryl derivatives of the present invention are represented by the following general formula (1): one example is 2-amino-2-[4-(3-benzyloxyphenoxy)-2-chlorophenyl]propyl-1,3-propanediol.Type: GrantFiled: September 25, 2002Date of Patent: November 8, 2005Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Yasushi Kohno, Naoki Ando, Takahiro Tanase, Kazuhiko Kuriyama, Satoru Iwanami, Shinji Kudou
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Patent number: 6521667Abstract: The present invention features calcilytic compounds. “Calcilytic compounds” refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.Type: GrantFiled: August 11, 1998Date of Patent: February 18, 2003Assignees: NPS Pharmaceuticals, Inc., SmithKline Beecham, PLC, SmithKline Beecham, Corp.Inventors: Eric G. Del Mar, Robert M. Barmore, Derek Sheehan, Bradford C. Van Wagenen, James F. Callahan, Richard M. Keenan, Nikesh R. Kotecha, Maria Amparo Lago, Linda Sue Southall, Mervyn Thompson
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Patent number: 6376711Abstract: The invention relates to a method for preparing aryl ethers that are useful as antidepressants. The invention also relates to intermediates useful in the method and to methods for preparing such intermediates.Type: GrantFiled: December 23, 1999Date of Patent: April 23, 2002Assignee: Pharmacia and Upjohn CompanyInventors: Kevin E. Henegar, Sarah E. Mancini, Keith D. Maisto
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Patent number: 6239313Abstract: The invention relates to a process for the solid state synthesis of enantiopure &bgr;-aminoalcohols by preparing inclusion complexes of aryloxyepoxide with cyclodextrin by adding an epoxide in equimolar ratio in an organic solvent to an aqueous solution of cyclodextrin, reacting the cyclodextrin complex of aryloxyepoxide with a nucleophile in solid state by intimately grinding the mixture using a mortar and pestle, continuing the mixing till the starting epoxide disappeared on tic, removing excess amines under vacuum, extracting the &bgr;-aminoalcohols produced with a solvent with yields of more than 50% and enantioselectivity of upto 100%.Type: GrantFiled: March 24, 2000Date of Patent: May 29, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Rama Rao Kakulapati, Bhanumathi Nanduri, Rajender Reddy Eleti
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Patent number: 6025517Abstract: A synthesis of fluoxetine is disclosed. The process begins with benzoylacetonitrile, which is reduced, optionally in the presence of a chiral ligand, to produce the corresponding aminoalcohol, and the amine is carbamoylated without isolation. The alcohol is deprotonated and reacted with 4-chloro- or 4-fluoro benzotrifluoride or with 4-trifluoromethylphenol to provide a carbamate of fluoxetine. The carbamate is reduced with a hydride or with borane to provide fluoxetine free base. The process may be employed for the synthesis of individual enantiomers of fluoxetine.Type: GrantFiled: August 3, 1998Date of Patent: February 15, 2000Assignee: Sepracor Inc.Inventors: James Wallace Hilborn, Alex Roger Jurgens
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Patent number: 6022894Abstract: The present invention features calcilytic compounds. "Calcilytic compounds" refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.Type: GrantFiled: April 4, 1997Date of Patent: February 8, 2000Assignees: NPS Pharmaceuticals, Inc., SmithKline Beecham, Corp., SmithKline Beecham, PLCInventors: Eric G. Del Mar, Robert M. Barmore, Derek Sheehan, Bradford C. Van Wagenen, James F. Callahan, Richard M. Keenan, Nikesh R. Kotecha, Maria Amparo Lago, Linda Sue Southall, Mervyn Thompson
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Patent number: 5723489Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 to R.sup.9 are as defined herein and m is the integer 0 or 1.These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.Type: GrantFiled: May 7, 1996Date of Patent: March 3, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Philip M. Sher, William N. Washburn, Kathleen M. Poss
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Patent number: 5618968Abstract: The invention provides the preparation procedure for N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine having the general formula (I), where R is hydrogen and the group of the general formula (II), in which R.sub.1 is aryl, alkylaryl and alkyl group with C.sub.1 to C.sub.4 atoms, and n is 0 and 1, and also covers the compounds of the general formula (I), where R is the group of the formula (II), in which R.sub.1 is aryl and alkylaryl group, and n is 0 and 1.According to this invention by condensation of N-substituted derivatives of N-methyl-3-phenyl-3-hydroxypropylamine (XV), where R.sub.1 is benzyl and p-nitrobenzyl group and n is 0, and p-trifluoromethylchlorbenzene (XVI) prepared N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine (I), where R is the group of the formula (II), in which n and R are the same as in the compound (XV), which by the reaction with chloroformic acid esther (XVII), where R.sub.Type: GrantFiled: November 3, 1993Date of Patent: April 8, 1997Assignee: PLIVA Farmaceutska kemijska, Prehrambena i kozmeticka industrija, dionicko drustvoInventors: Zdravko Crnic, Srecko I. Kirin
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Patent number: 5482964Abstract: Substituted phenoxyhydroxy amines and derivatives thereof are described as well as methods for the preparation and pharmaceutical compositions of same, which are central nervous system agents useful in the treatment of neurological disorders including traumatic brain surgery, stroke, migraine, acute and chronic pain, epilepsy, Parkinson's disease, Alzheimer's disease, amyotropic lateral sclerosis, multiple sclerosis, psychosis, and depression.Type: GrantFiled: October 11, 1994Date of Patent: January 9, 1996Assignee: Warner-Lambert CompanyInventor: Sheryl J. Hays
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Patent number: 5187190Abstract: Compounds of the formula (I): ##STR1## wherein R.sup.1 is hydrogen or fluoro and R.sup.2 is hydrogen or C1-6 alkyl and salts thereof are described as agents for the treatment of obesity and related conditions. Processes for their preparation and intermediates are described.Type: GrantFiled: November 2, 1990Date of Patent: February 16, 1993Assignee: Imperial Chemical Industries PLCInventor: David J. Lecount
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Patent number: 5166218Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.Type: GrantFiled: August 12, 1991Date of Patent: November 24, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Marcel Muller
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Patent number: 5047425Abstract: Compounds of the formula ##STR1## wherein Ar, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the meanings mentioned in the description, processes and intermediates for their preparation, pharmaceutical compositions which contain them and their use in therapy in the treatment of cardiovascular diseases.Type: GrantFiled: November 30, 1988Date of Patent: September 10, 1991Assignee: Simes Societa Italiana Medicinali & Sintetici SpAInventors: Cesare Casagrande, Francesco Santangelo, Luisa Calabi
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Patent number: 4864061Abstract: New substituted phenoxyalkanolamines and phenoxyalkanol-cycloalkylamines of the general formula I ##STR1## in which R.sup.1 and R.sup.2, which can be identical or different, denote alkyl groups with in each case 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together denote the group --(CH.sub.2).sub.n --, wherein n is the number 4 or 5, R.sup.3 denotes hydrogen, or an alkyl group or an acyl group with in each case 1 to 6 carbon atoms, R.sub.4 denotes an alkyl group with 1 to 4 carbon atoms or the cyclopropylmethyl group and R.sup.5 denotes hydrogen halogen or alkyl, and acid addition salts thereof, have a cardioselective .beta..sub.1 -adrenolytic and hypotensive action. They can be used as medicaments for the treatment of angina pectoris, hypertension and arrhythmias.Type: GrantFiled: July 8, 1986Date of Patent: September 5, 1989Assignee: Beiersdorf AktiengesellschaftInventor: Erich Cohnen
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Patent number: 4772631Abstract: The invention concerns a series of novel phenoxyacetic acid ethers (and pharmaceutically acceptable salts thereof) of the formula I in which R.sup.1 is H or F, R.sup.2 and R.sup.3 are H or (1-3C)alkyl, Z is CH.sub.2 OH or a group --CO.R.sup.4 in which R.sup.4 is OH, NH.sub.2 or (1-6C)alkoxy. The invention also includes pharmaceutical compositions for use in treating obesity and related conditions and provides processes for the manufacture of the novel ethers.Type: GrantFiled: July 28, 1986Date of Patent: September 20, 1988Assignee: Imperial Chemical Industries PlCInventors: Brian R. Holloway, Ralph Howe, Balbir S. Rao, Donald Stribling
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Patent number: 4665094Abstract: Hydroxyalkyl-phenoxy-propan-2-olamines and novel esters thereof are oculoselective .beta.-blockers useful in the treatment of elevated intraocular pressure with little or no effect on the pulmonary or cardiovascular system.Type: GrantFiled: August 29, 1985Date of Patent: May 12, 1987Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello
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Patent number: 4652584Abstract: Phenoxypropanol derivatives having a 2-acetylenic moiety on the phenyl group thereof of the following formula (I): ##STR1## and their use as anti-hypertensives, e.g. in man. Also part of the invention are pharmaceutical compositions and intermediates used in the synthesis.Type: GrantFiled: July 13, 1984Date of Patent: March 24, 1987Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4435426Abstract: The present invention relates to novel products, responding to general formula: ##STR1## in which R.sub.1 and R.sub.2 taken together represent an atom of oxygen .dbd.O or R.sub.1 represents hydrogen and R.sub.2 represents an OH radical, R.sub.3 designates an atom of hydrogen or a straight or branched alkyl radical, or an alkynyl group having from 1 to 6 atoms of carbon, R.sub.4 represents a straight or branched alkyl radical having from 1 to 6 atoms of carbon, R.sub.5 designates an atom of hydrogen, an alkyl group having from 1 to 4 atoms of carbon or an acylamine group and n=3 or 4; as well as to the acid addition salts of said products, to a process for preparing said products and to drugs, particularly active on the cardiovascular system, containing at least one of said products.Type: GrantFiled: May 25, 1982Date of Patent: March 6, 1984Assignee: Societe Anonyme dite: SanofiInventors: Henri Demarne, Jean Wagnon
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Patent number: 4356322Abstract: A series of novel derivatives of phenoxyalkanolamine of the general formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are hydrogen, alkyl of 1 to 2 carbon atoms, methoxy, halogen, nitro, amino or acylamino residues, and the salts thereof, are described, as are methods for their synthesis. The compounds are highly active .beta..sub.1 -specific sympathicomimetics with a partially antagonistic component.Type: GrantFiled: March 24, 1980Date of Patent: October 26, 1982Assignee: Veb Arzneimittelwerk DresdenInventors: Dieter Lehmann, Klaus Femmer, Gottfried Faust
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Patent number: 4336267Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.Type: GrantFiled: May 19, 1980Date of Patent: June 22, 1982Assignee: Aktiebolaget HassleInventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
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Patent number: 4322437Abstract: The present invention relates to a compound of formula I, ##STR1## wherein A is straight chain alkylene of 2 to 4 carbon atoms, or straight chain alkenylene of 2 to 4 carbon atoms,n is 1, 2 or 3,R is hydrogen or halogen of atomic number from 9 to 35, andeither (i) R.sub.1 is a group of formula II, ##STR2## wherein R.sub.2 and R.sub.3, independently, are hydrogen or alkyl of 1 to 4 carbon atoms, andR.sub.4 is alkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 5 carbon atoms, alkylthioalkyl of 2 to 5 carbon atoms, phenylalkyl or phenoxyalkyl or phenylthioalkyl, wherein the alkyl moiety has from 1 to 3 carbon atoms, or phenyl, the phenyl ring of each of the last four radicals being unsubstituted or mono-substituted by, or disubstituted independently by, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, hydroxy or halogen of atomic number from 9 to 35, andR.sub.5 is hydrogen,or (ii) R.sub.1 and R.sub.Type: GrantFiled: May 10, 1977Date of Patent: March 30, 1982Assignee: Sandoz Ltd.Inventors: Richard Berthold, Trevor G. Payne
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Patent number: 4302601Abstract: The present invention relates to phenoxypropane having the formula ##STR1## in which R.sup.1 and R.sup.2 are like or unlike and each is an alkyl group having 1-4 carbon atoms, R.sup.3 is hydrogen or an alkyl group having 1-4 carbon atoms, R.sup.4 is a halogen atom, preferably fluorine, chlorine or bromine, including their optical isomers and also their addition salts with acids.These compounds are of therapeutic value in the treatment of cardiovascular conditions.The invention also relates to methods of synthesis of these products including a synthesis which involves the production, as a intermediate of an 8-aza-4,9-dioxa-2,3-benzo-bicyclo-[4,2,1]-octane having the formula ##STR2## in which R.sup.1 and R.sup.4 are as above defined.Type: GrantFiled: March 12, 1980Date of Patent: November 24, 1981Assignee: C M IndustriesInventor: Henri Demarne
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Patent number: 4275058Abstract: 1-Indanyloxy- or tetrahydronaphthyloxy-3-amino-2-butanol derivatives, especially erythro-1-(7-methylindan-4-yloxy)-3-isopropylaminobutan-2-ol, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess peripherally-selective .beta.-adrenergic blocking activity.Type: GrantFiled: February 5, 1979Date of Patent: June 23, 1981Assignee: Imperial Chemical Industries LimitedInventor: Howard Tucker
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Patent number: 4252825Abstract: Compositions having therapeutic value in the treatment of cardiovascular conditions associated with the overproduction of catecholamines include as the active ingredient 5-fluoro-2-(2-hydroxy-3-tertiary butyl-amino-propoxy) butyrophenone-, its optical isomers and non-toxic acid addition salts.Type: GrantFiled: January 5, 1979Date of Patent: February 24, 1981Assignee: C. M. IndustriesInventor: Henri Demarne